N-methyl-2-pyrrolidone → (R)-3-isopropyl-6-((2,2,2-trifluoro-1-phenylethyl)amino)pyrimidine-2,4(1H,3H)-dione

HRID 709431

반응식

HRID 709431 반응식
Cl[C:2]1[NH:7][C:6](=[O:8])[N:5]([CH:9]([CH3:11])[CH3:10])[C:4](=[O:12])[CH:3]=1.[F:13][C:14]([F:24])([F:23])[C@@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH2:16].CN1C(=O)CCC1>O.CC#N>[CH:9]([N:5]1[C:4](=[O:12])[CH:3]=[C:2]([NH:16][C@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([F:13])([F:23])[F:24])[NH:7][C:6]1=[O:8])([CH3:11])[CH3:10]

참가 물질

5

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 8201076-Chloro-3-(propan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dioneHCID 11789718(alphaR)-alpha-(Trifluoromethyl)benzenemethanamine

생성물 1

HCID 117761995(R)-3-isopropyl-6-((2,2,2-trifluoro-1-phenylethyl)amino)pyrimidine-2,4(1H,3H)-dione수율 34%

시약·촉매·용매 1

HCID 18373917Acetonitrile--water (1/1)용매

반응 조건

온도
180 °C

실험 절차

To a 0.2-0.5 mL microwave vial was added 1.3 (85 mg, 0.45 mmol) and (R)-2,2,2-trifluoro-1-phenylethan-1-amine (200 uL, excess). The reaction mixture sealed and heated at 180° C. in a microwave reactor for 40 minutes. The reaction mixture was cooled to ambient temperature and then NMP (1 mL) was added to completely dissolve the solid. Next, a 2:1 H2O/CH3CN mixture (6 mL) was added which resulted in precipitation. The solid was isolated by filtration, washed with H2O and dried to give 50 mg (34%) of the title compound as a white solid. LC/MS: m/z (ES+) 328 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): δ ppm 9.79 (br s, 1H), 7.50-7.40 (m, 5H), 5.66-5.56 (m, 2H), 4.92-4.87 (m, 2H), 1.28-1.25 (m, 6H).

후처리

  1. customThe reaction mixture sealed
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. dissolutionto completely dissolve the solid
  4. customresulted in precipitation
  5. customThe solid was isolated by filtration
  6. washwashed with H2O
  7. customdried

출처 및 근거

ORD 기록
ord-704fa07b54ac49bd84a9a13a44c6d232
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181200B2

연결된 노트

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