Triethylamine → 6-(2-Methoxyphenyl)-2-(methylthio)pyrimidine-4-carboxamide

HRID 68294Notes

Reaction equation

HRID 68294 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[C:13]([S:15][CH3:16])[N:12]=[C:11]([C:17]([OH:19])=O)[CH:10]=1.C([N:22](CC)CC)C.[Cl-].[NH4+].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[C:13]([S:15][CH3:16])[N:12]=[C:11]([C:17]([NH2:22])=[O:19])[CH:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2724699PyBOPHCID 393752796-(2-Methoxyphenyl)-2-(methylthio)pyrimidine-4-carboxylic acid

Product 1

HCID 588726496-(2-Methoxyphenyl)-2-(methylthio)pyrimidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 6-(2-methoxyphenyl)-2-(methylthio)pyrimidine-4-carboxylic acid (9.8 g, 40 mmol), triethylamine (33 mL, 240 mmol), and ammonium chloride (11 g, 200 mmol) in DMF (40 mL) was added PyBOP (21.9 g, 42 mmol) in five portions. The reaction was complete in 2 h, as determined by LCMS analysis. The reaction mixture was poured into water (1.5 L) and stirred for 10 minutes. The precipitate was collected by filtration and dried overnight under high vacuum to give 6-(2-methoxyphenyl)-2-(methylthio)pyrimidine-4-carboxamide. 1H NMR (300 MHz, CDCl3) δ 8.40 (s, 0.7H), 8.05 (m, 1.3H), 7.74 (bs, 1H), 7.44 (m, 1H), 7.05 (m, 2H), 5.78 (bs, 1H), 3.92 (s, 3H); 2.65 (s, 3H). HPLC ret. time 2.71 min, 10-100% CH3CN, 5 min gradient; ESI-MS m/z 245.9 (M+H)+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-de42c27c4d3f4307a5aa952636231542
Source dataset
uspto-grants-2014_09
Patent number
US08822451B2

Reaction notes

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