4-Chloro-6-methyl-2-(pyrrolidin-1-yl)pyrimidine → HCID 57829863, compound

HRID 1855513Notes

Reaction equation

HRID 1855513 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.Cl[C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:18]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:17]2[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[N:18]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

3

Reactant 2

HCID 177508834-Chloro-6-methyl-2-(pyrrolidin-1-yl)pyrimidineHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline

Product 1

HCID 57829863HCID 57829863, compoundYield 58%

Procedure

The title compound was prepared from 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine (61 mg, 0.30 mmol) and 4-chloro-6-methyl-2-pyrrolidin-1-yl-pyrimidine (65 mg, 0.33 mmol, example 95a) in analogous manner as described in example 90. The crude product was purified by stirring with diethyl ether. It was obtained in 58% yield as a light brown solid. MS ISP (m/e): 365.3 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.30 (s, 1H), 8.06 (s, 1H), 7.65 (s, 1H), 7.21 (d, 1H), 7.15 (d, 1H), 7.02 (s, 1H), 5.91 (s, 1H), 3.81 (s, 3H), 3.50 (br m, 4H), 2.15 (s, 3H), 2.14 (s, 3H), 1.90 (br m, 4H).

Workup

  1. customThe crude product was purified
  2. customIt was obtained in 58% yield as a light brown solid

Sources & evidence

ORD record
ord-88621551233e4e0cbd8be791b4d1438a
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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