1,2-Dichloroethane → 2-(Methylthio)-6-phenylpyrimidine-4-carboxamide

HRID 68298

반응식

HRID 68298 반응식
C[N:2]1CCOCC1.[CH3:8][S:9][C:10]1[N:15]=[C:14]([C:16](O)=[O:17])[CH:13]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:11]=1.[Cl-].[NH4+].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH3:8][S:9][C:10]1[N:15]=[C:14]([C:16]([NH2:2])=[O:17])[CH:13]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:11]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 393492022-(Methylthio)-6-phenylpyrimidine-4-carboxylic acid

생성물 1

HCID 588727612-(Methylthio)-6-phenylpyrimidine-4-carboxamide수율 94.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

N-Methylmorpholine (2.31 mL, 21 mmol) was added dropwise by syringe to a mixture of 2-methylsulfanyl-6-phenylpyrimidine-4-carboxylic acid (3.45 g, 14 mmol), ammonium chloride (4.27 g, 80 mmol), HOBt (2.84 g, 21 mmol), and EDC (4.0 g, 21 mmol) in DMF (40 mL) at room temperature. The reaction solution was stirred at room temperature for 3 h before the DMF was removed by rotary evaporation. Column chromatography (SiO2, DCM/EtOAc 5:1) afforded 3.23 g of 2-(methylthio)-6-phenylpyrimidine-4-carboxamide as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.25 (m, 2H), 8.13 (s, 1H), 7.59 (m, 3H), 2.62 (s, 3H). HPLC ret. time 2.71 min, 10-100% CH3CN, 5 min gradient. ESI-MS m/z 246.1 (M+H)+.

후처리

  1. customwas removed by rotary evaporation

출처 및 근거

ORD 기록
ord-7f173a098f5a4026aa5fcce250a12d7a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822451B2

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