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

HRID 68294

반응식

HRID 68294 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-de42c27c4d3f4307a5aa952636231542
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822451B2

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