Water → 4-(2-Hydroxy-2-phenylethylamino)-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

HRID 348500Notes

Reaction equation

HRID 348500 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[C:22](Cl)=[N:23][C:24]([S:27][CH3:28])=[N:25][CH:26]=2)=[O:20])=[CH:14][CH:13]=1.O>CO>[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[C:22]([NH:1][CH2:2][CH:3]([OH:4])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[N:23][C:24]([S:27][CH3:28])=[N:25][CH:26]=2)=[O:20])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1000PhenylethanolamineHCID 188588054-Chloro-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

Product 1

HCID 867604054-(2-Hydroxy-2-phenylethylamino)-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amideYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-1-phenyl-ethanol (140 mg, 1.01 mmol) in methanol (5 mL) was added 4-chloro-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (100 mg, 0.34 mmol). The mixture was stirred for 16 h at an ambient temperature and the resulting mixture was poured into water. Solids were collected by filtration and were dried in vacuo to afford 103.7 mg (0.26 mmol, 78% yield) of the titled compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.22(s, 1H), 8.85 (m, 1H), 8.60 (s, 1H), 7.65(m, 2H), 7.40–7.05 (m, 7H), 5.67 (m, 1H), 4.78 (m, 1H), 3.78 (m, 1H), 3.41 (m, 1H), 2.44 (s, 31H); MS (EI) m/z 397.18 (M−H)−.

Workup

  1. filtrationSolids were collected by filtration
  2. customwere dried in vacuo

Sources & evidence

ORD record
ord-81bdd0bb2ea94c2eaf06ecd22be1d8ae
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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