2-Fluorobenzylamine → HCID 58166445, compound

HRID 1405989Notes

Reaction equation

HRID 1405989 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.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][NH2:26]>CO>[F:11][C:10]1[C:5]([NH:26][CH2:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[F:18])=[N:6][C:7](=[O:17])[N:8]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 666492-FluorobenzylamineHCID 58166405HCID 58166405, compound

Product 1

HCID 58166445HCID 58166445, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(allylthio)-5-fluoro-1-(thiophen-3-yl)pyrimidin-2(1H)-one (140 mg, 0.66 mmol) in MeOH (1 mL) was added (2-fluorophenyl)methanamine (50 mg, 0.186 mmol). The reaction mixture was heated at 100° C. for 30 min in a microwave. After cooling, the mixture was purified by preparative thin layer chromatography to give 5-fluoro-4-(2-fluorobenzylamino)-1-(thiophen-3-yl)pyrimidin-2(1H)-one (41 mg, 20%) as a white solid: mp 75-78° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.70 (s, 1H), 8.16 (d, J=7.0 Hz, 1H), 7.66 (dd, J=3.2, 1.4 Hz, 1H), 7.57 (dd, J=5.2, 3.2 Hz, 1H), 7.43-7.13 (m, 5H), 4.63 (d, J=5.5 Hz, 2H); ESIMS m/z 320 ([M+H]+).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-051487d0367f41e0b18689e56aa052e8
Source dataset
uspto-grants-2014_12
Patent number
US08916579B2

Reaction notes

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