Ammonia → HCID 58166466, compound

HRID 1405987Notes

Reaction equation

HRID 1405987 reaction equation
C(S[C:5]1[C:10]([F:11])=[CH:9][N:8]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[C:7](=[O:17])[N:6]=1)C=C.[NH3:18]>CO>[NH2:18][C:5]1[C:10]([F:11])=[CH:9][N:8]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[C:7](=[O:17])[N:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 58166405HCID 58166405, compound

Product 1

HCID 58166466HCID 58166466, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

This material was prepared by the procedure described in J. Org. Chem. 2006, 71, 9183-9190. 4-(Allylthio)-5-fluoro-1-(thiophen-3-yl)pyrimidin-2(1H)-one (330 mg, 1.23 mmol) was dissolved in a methanol solution of ammonia (7 N, 5 mL). The reaction mixture was stirred overnight at 100° C. in a pressure vessel. After removal of solvent, the residue was purified by preparative thin layer chromatography to give 4-amino-5-fluoro-1-(thiophen-3-yl)pyrimidin-2(1H)-one (177 mg, 68%) as a yellow solid: mp 228-229° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.11 (d, J=6.9 Hz, 1H), 7.89 (s, 1H), 7.65 (d, J=1.9 Hz, 2H), 7.56 (dd, J=5.1, 3.3 Hz, 1H), 7.29 (dd, J=5.1, 1.0 Hz, 1H); ESIMS m/z 212 ([M+H]+).

Workup

  1. customThis material was prepared by the procedure
  2. customAfter removal of solvent
  3. customthe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-94ccc7eb28c04eb29f57e48e9cadd664
Source dataset
uspto-grants-2014_12
Patent number
US08916579B2

Reaction notes

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