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

HRID 709431

反応式

HRID 709431 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

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

反応条件

温度
180 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-704fa07b54ac49bd84a9a13a44c6d232
出典データセット
uspto-grants-2015_11
特許番号
US09181200B2

関連ノート

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