Acetyl chloride → HCID 19787908, compound

HRID 1656533Notes

Reaction equation

[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:20]([CH3:22])[CH3:21])[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[O:11])[C:5]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[N:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:34](Cl)(=[O:36])[CH3:35].C(OCC)(=O)C>O1CCCC1>[C:34]([NH:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:20]([CH3:21])[CH3:22])[C:14](=[O:19])[C:15]([F:16])([F:17])[F:18])=[O:11])[C:5]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[N:4][CH:3]=1)(=[O:36])[CH3:35]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-[5-amino-6-oxo-2-(2-thienyl)-1,6-dihydro-1-pyrimidinyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.3 g) in tetrahydrofuran (7 mL) was added sodium carbonate (0.4 g) and the mixture cooled in an ice bath to 0° C. Acetyl chloride (0.11 mL) was added and the solution warmed to room temperature and let stir for 1 h. The mixture was poured into ethyl acetate and washed (1N HCl, a saturated solution of sodium carbonate, and H2O). The resulting solution was dried and the solvent removed by evaporation. The resulting material was purified by chromatography, eluting with methanol:dichloromethane (gradient, 5:95, 12:88) to give the title compound (0.46 g) as a light yellow powder; TLC: Rf =0.47, methanol:dichloromethane (5:95); NMR (DMSO/D2O): 8.77 (s,1), 7.81 (d,1), 7.36 (d,1), 7.09 (t,1), 4.83 (m,2), 4.09 (d,1), 2.26 (m, 1), 2.13 (s,3), 0.93 (d,3), 0.80 (d,3).

Workup

temperaturethe solution warmed to room temperature
washwashed (1N HCl
customThe resulting solution was dried
customthe solvent removed by evaporation
customThe resulting material was purified by chromatography
washeluting with methanol

Sources & evidence

ORD record: ord-7c6c50402c48420f9da7fc4a0e6a78a0
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254558

Reaction notes

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