4-(2-chloro-6-methylpyrimidin-4-yl)morpholine → HCID 57829825, compound

HRID 1855439Notes

Reaction equation

HRID 1855439 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[N:22]=[C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:20]=[C:19]([CH3:29])[N:18]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:17]2[N:18]=[C:19]([CH3:29])[CH:20]=[C:21]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[N:22]=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 31569994-(2-chloro-6-methylpyrimidin-4-yl)morpholineHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline

Product 1

HCID 57829825HCID 57829825, compoundYield 87%

Procedure

The title compound was prepared from 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine (61 mg, 0.30 mmol) and 4-(2-chloro-6-methyl-pyrimidin-4-yl)-morpholine (71 mg, 0.33 mmol) in analogous manner as described in example 90. The crude product was purified by stirring with diethyl ether. It was obtained in 87% yield as a light brown solid. MS ISP (m/e): 381.3 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.27 (s, 1H), 7.90 (s, 1H), 7.63 (s, 1H), 7.23 (d, 1H), 7.16 (d, 1H), 7.01 (s, 1H), 6.21 (s, 1H), 3.77 (s, 3H), 3.68 (m, 4H), 3.57 (m, 4H), 2.22 (s, 3H), 2.14 (s, 3H).

Workup

  1. customThe crude product was purified
  2. customIt was obtained in 87% yield as a light brown solid

Sources & evidence

ORD record
ord-61349c0fead647869b8f658ccb5a5b86
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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