2-Chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine → HCID 71577881, compound

HRID 2283514Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH2:5].Cl[C:15]1[N:20]=[C:19]([NH:21][CH3:22])[C:18]([C:23]([F:26])([F:25])[F:24])=[CH:17][N:16]=1>C(O)CCC.C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH:5][C:15]1[N:20]=[C:19]([NH:21][CH3:22])[C:18]([C:23]([F:26])([F:24])[F:25])=[CH:17][N:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 2-methoxy-4-(methylsulfonyl)aniline (0.095 g, 0.47 mmol) and 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (0.10 g, 0.47 mmol) in 1-butanol (1.5 mL) was added TFA (0.036 mL, 0.047 mmol). The reaction was stirred in a sealed tube at 100° C. for 1.5 h. The reaction was concentrated and the product was isolated by reverse-phase HPLC to give N2-(2-methoxy-4-(methylsulfonyl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine (0.18 g, 20%). 1H NMR (400 MHz, DMSO) δ 8.58 (d, J=12.9, 1H), 8.24 (d, J=5.0, 2H), 7.53 (d, J=10.1, 1H), 7.48 (s, 1H), 7.38-7.29 (m, 1H), 3.99 (s, 3H), 3.20 (s, 3H), 2.94 (d, J=4.3, 3H); LRRK2 Ki=0.002.

Workup

concentrationThe reaction was concentrated
customthe product was isolated by reverse-phase HPLC

Sources & evidence

ORD record: ord-ea854a0bcaca4c98848b209b2578952c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145402B2

Reaction notes

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