2-Chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine → HCID 71577748, compound

HRID 2401492Notes

Reaction equation

[NH2:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH3:12])[CH2:5]2.Cl[C:16]1[N:21]=[C:20]([NH:22][CH3:23])[C:19]([C:24]([F:27])([F:26])[F:25])=[CH:18][N:17]=1>CC(O)(C)C>[CH3:14][O:13][C:3]1[C:2]([NH:1][C:16]2[N:21]=[C:20]([NH:22][CH3:23])[C:19]([C:24]([F:27])([F:25])[F:26])=[CH:18][N:17]=2)=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([CH3:12])[C:7]2=[O:11]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-amino-4-methoxy-2-methylisoindolin-1-one (81 mg, 0.42 mmol) in t-BuOH (3 mL) was added 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (89 mg, 0.42 mmol). The mixture was heated at 100° C. for 1 h under microwave irradiation. The solvent was evaporated in vacuo and the residue was purified by reverse-phase prep-HPLC to afford the title compound as a white solid (35 mg, yield 23%). m/z (ES+APCI)+: [M+H]+368.1. 1H-NMR (Bruker, 500 MHz, MeOD) δ 8.65 (d, J=8.5 Hz, 1H), 8.13 (s, 1H), 7.43 (d, J=8.5 Hz, 1H), 4.69 (s, 2H), 4.06 (s, 3H), 3.19 (s, 3H), 3.05 (s, 3H)

Workup

customThe solvent was evaporated in vacuo
customthe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record: ord-f7b2f80e9d7b430a8cb8d922eb5a8755
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796296B2

Reaction notes

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