Hydrochloric Acid → N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

HRID 63123

반응식

HRID 63123 반응식
Cl[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1.[CH:18]1([NH2:23])[CH2:22][CH2:21][CH2:20][CH2:19]1.Cl>C(#N)C.O1CCOCC1.O>[CH:18]1([NH:23][C:2]2[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[N:3]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 2906CyclopentylamineHCID 832906664-chloro-5,6-dimethyl-N-(pyridin-2-ylmethyl)pyrimidin-2-amine

생성물 1

HCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine수율 19%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 312751,4-Dioxane용매

실험 절차

A solution of 4-chloro-5,6-dimethyl-N-(pyridin-2-ylmethyl)pyrimidin-2-amine (200 mg, 0.8 mmol, Step C) and cyclopentanamine (85 mg, 1 mmol) in acetonitrile (5 mL) was treated with 3.5 M hydrogen chloride in dioxane (0.2 mL), and the resultant mixture was refluxed overnight. The reaction mixture was diluted with water (50 mL), and the resultant precipitate was collected by filtration. The precipitate was purified by crystallization from ethanol (10 mL) to afford 42 mg (19%) of the titled compound as the hydrochloride salt as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.40-1.50 (m, 4H), 1.50-1.67 (m, 4H), 1.88 (s, 3H), 2.27 (s, 3H), 4.00-4.12 (m, 1H), 4.92 (d, J=4.57 Hz, 2H), 7.71-4.83 (m, 2H), 7.83 (d, J=8.06 Hz, 1H), 8.17-8.25 (m, 1H), 8.33-8.39 (m, 1H), 8.76 (d, J=5.10 Hz, 1H), 13.24 (bs, 1H); MS (ESI) m/z 398.5 (ESI) (M+1)+.

후처리

  1. filtrationthe resultant precipitate was collected by filtration
  2. customThe precipitate was purified by crystallization from ethanol (10 mL)

출처 및 근거

ORD 기록
ord-cabe21ce45014e838310764bc8e721f3
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447051B2

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