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

HRID 63123

反応式

HRID 63123 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 312751,4-Dioxane溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-cabe21ce45014e838310764bc8e721f3
出典データセット
uspto-grants-2016_09
特許番号
US09447051B2

関連ノート

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