Pyrrolo[1,2-a]pyrimidine-6-carboxylic acid, 4,6,7,8-tetrahydro-4-oxo-3-[[(phenylmethoxy)carbonyl]amino]-, (6S)- synthesis
- Product Name:Pyrrolo[1,2-a]pyrimidine-6-carboxylic acid, 4,6,7,8-tetrahydro-4-oxo-3-[[(phenylmethoxy)carbonyl]amino]-, (6S)-
- CAS Number:227616-77-5
- Molecular formula:C16H15N3O5
- Molecular Weight:329.31
227616-76-4
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227616-77-5
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Yield:227616-77-5 95%
Reaction Conditions:
with water;trifluoroacetic acid in dichloromethane at 20;
Steps:
1.H Step H: (S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic Acid (1 h)
tert-Butyl ester 1 g (11.13 g, 28.9 mmol) was dissolved in 1:1 CH2Cl2/TFA. 1 mL H2O was added and the mixture was stirred overnight at rt. The mixture was concentrated and the resultant residue was co-evaporated with CCl4 (3*). The residual oil was triturated with 1:1 Et2O/hexanes (100 mL) and the solid (9.0 g, 95%) was collected and dried, to provide 1 h. 1H NMR (300 MHz, CDCl3) δ 8.69 (br s, 1H), MS (ESI) 330.3 (M+H+); 328.3 (M-H+).
References:
US2004/6065,2004,A1 Location in patent:Page/Page column 21