4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine synthesis
- Product Name:4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine
- CAS Number:479633-63-1
- Molecular formula:C13H10ClN3O2S
- Molecular Weight:307.76
Yield:479633-63-1 97%
Reaction Conditions:
with sodium hydroxide in water;acetone at 0 - 20; for 6 h;
Steps:
1.1
EXAMPLE 13-((3Λ,4Λ)-4-Methyl-3-(methyl(7H-pyrrolo[2,3-rf]pyrimidin-4- yl)amino)piperidin-l-yl)-3-oxopropanenitrile mono citrate salt (CP-690550 citrate salt)Step 1[00151] 4-Chloro-7-tosyl-7H-pyrrolor2,3-6?pynmidine: At about O 0C, sodium hydroxide (2 mol/L in water, 8 mL, 1.20 equiv.) was added to a solution of 4- methylbenzene-1-sulfonyl chloride (2.7 g, 13.9 mmol, 1.10 equiv.) and 4-chloro- 7H-pyrrolo[2,3-J]pyrimidine (2 g, 12.8 mmol, 1.00 equiv.) in acetone (20 mL). The resulting solution was stirred at about 20 0C for about 6 hours. The solids were collected by filtration and washed with acetone/water to give the title product as a white solid (4.0 g; yield = 97%). 1H NMR (300 MHz, CDCl3) δ: 8.78 (s, IH), 8.11 (d, J = 8.4 Hz, 2H), 7.80 (d, J = 4.2 Hz, IH), 7.34 (d, J = 8.4 Hz, 2H), 7.73 (d, J = 4.2 Hz, IH), 2.42 (s, 3H). LC-MS: m/z = 308/310 (M+H)+.
References:
WO2010/123919,2010,A2 Location in patent:Page/Page column 49
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