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

HRID 709431

Reaction equation

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]

Participants

Conditions

Temperature: 180 °C

Procedure

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).

Workup

customThe reaction mixture sealed
temperatureThe reaction mixture was cooled to ambient temperature
dissolutionto completely dissolve the solid
customresulted in precipitation
customThe solid was isolated by filtration
washwashed with H2O
customdried

Sources & evidence

ORD record: ord-704fa07b54ac49bd84a9a13a44c6d232
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181200B2

Linked notes

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