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CAS No. : | 7036-04-6 | MDL No. : | MFCD04115728 |
Formula : | C4H5NOS | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | WQVOUANKVCYEIQ-UHFFFAOYSA-N |
M.W : | 115.15 | Pubchem ID : | 2763215 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethylsulfide borane complex; In tetrahydrofuran; at 0℃; for 24h; | 164 2-( 1 H-Indazol-4-yl V4-morpholin-4-yl-6-(4-thiazol-4-ylmethyl-piperazin- 1 - ylmethyl)-thieno[3,2-d1pyrimidine.Via 2-chloro-4-mophiholin-4-yl-6-(4-thiazol-4-ylmethyl-piperazin- 1 - ylmethyl)-thieno[3,2-d]pyrimidine, prepared from l-thiazol-4-ylmethyl-pirhoerazine, via 2-chloro-4-morpholin-4-yl-6-(4-thiazol-4-ylmethyl-piperazin- 1 -ylmethyl)- thieno[3,2-d]pyrimidine, prepared according to the following procedure: to a suspension of 4-thiazolecarboxylic acid (500mg) in THF (1OmL) was added borane- dimethylsulfide complex (0.73mL). After 24 h the mixture was cooled to O0C and quenched by the addition of 2M hydrochloric acid and extracted into ethyl acetate. The organic layers were washed with brine and dried (MgSO4). The solvent was evaporated and the residue stirred in DCM/MeOH overnight. The mixture was concentrated and the residue purified by flash chromatography to give thiazol-4-yl- methanol (173mg). To a solution of thiazol-4-yl-methanol (168mg) in DCM (5mL) was added triethylamine (0.33mL) followed by methanesulfonyl chloride (0.17mL) at O0C. The mixture was stirred at room temperature for 10 min and diluted with DCM, washed with brine and dried (MgSO4). The crude product was purified by flash chromatography to give methanesulfonic acid thiazol-4-yl methyl ester (263 mg). To a solution of 2-chloro-4-morpholin-4-yl-6-piperazin-l-ylmethyl-thieno[3,2- d]pyrimidine (300mg) and methanesulfonic acid thiazol-4-yl methyl ester (213 mg) in MeCN (1OmL) was added potassium carbonate (164 mg) and the mixture heated at 80 °C for 8 h. The cooled mixture was filtered, the solvent evaporated and the residue partitioned between DCM and water. The organic layer was washed with brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography to give the desired product (249mg). EPO <DP n="88"/>1H NMR (400MHz, CDCl3) 2.57 (br s, 4H), 3.71 (s, 2H), 3.79 (s, 2H), 3.85 (t, J=4.8Hz, 4H), 4.02 (t, J=4.8Hz, 4H), 7.13 (s, IH), 7.30 (s, IH), 7.43 (t, J=7.8Hz, IH), 7.51 (d, J=8.3Hz, IH), 8.21 (d, J=6.9Hz, IH), 8.71 (d, J=2.0Hz, IH), 8.95 (s, IH), 10.10 (br s, IH); MS (ESI+) 533.25 (MH+). | |
Example 11 : 2-(lH-Indol-4-vI)-4-morpholin-4-yl-6-(4-thiazoI-4-vImethvI- piperazin-l-ylmethyl)-thieno[3,2-d1pyrimidine; To a suspension of 4-thiazolecarboxylic acid (500 mg) in tetrahydrofuran (10 mL) was added borane-dimethylsulfide complex (0.73 mL). After 24 hours the mixture was cooled to 0 °C and quenched by the addition of 2M hydrochloric acid and extracted into ethyl acetate. The organic layers were washed with brine and dried (MgSO4). The solvent was evaporated and the residue stirred in dichloromethane- methanol overnight. The mixture was concentrated and the residue purified by flash chromatography to give thiazol-4-yl-methanol (173 mg). |
[ 50382-32-6 ]
(2,4-Dimethylthiazol-5-yl)methanol
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