Sodium Carbonate → 3-cyclopropyl-N-((2,4-dimethoxy-6-vinylpyrimidin-5-yl)methyl)-1-ethyl-1H-pyrazol-5-amine

HRID 80859

反応式

HRID 80859 の反応式
Cl[C:2]1[C:7]([CH2:8][NH:9][C:10]2[N:14]([CH2:15][CH3:16])[N:13]=[C:12]([CH:17]3[CH2:19][CH2:18]3)[CH:11]=2)=[C:6]([O:20][CH3:21])[N:5]=[C:4]([O:22][CH3:23])[N:3]=1.[CH3:24][C:25]1(C)C(C)(C)OB(C=C)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:17]1([C:12]2[CH:11]=[C:10]([NH:9][CH2:8][C:7]3[C:6]([O:20][CH3:21])=[N:5][C:4]([O:22][CH3:23])=[N:3][C:2]=3[CH:24]=[CH2:25])[N:14]([CH2:15][CH3:16])[N:13]=2)[CH2:19][CH2:18]1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86690292N-((4-chloro-2,6-dimethoxypyrimidin-5-yl)methyl)-3-cyclopropyl-1-ethyl-1H-pyrazol-5-amine

生成物 1

HCID 866902933-cyclopropyl-N-((2,4-dimethoxy-6-vinylpyrimidin-5-yl)methyl)-1-ethyl-1H-pyrazol-5-amine

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a solution of N-((4-chloro-2,6-dimethoxypyrimidin-5-yl)methyl)-3-cyclopropyl-1-ethyl-1H-pyrazol-5-amine (2.42 g, 7.16 mmol) in DME (50 mL) and water (15 mL) was added 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (2.5 mL, 14.3 mmol), Pd(Ph3P)4 (0.828 g, 0.716 mmol) and sodium carbonate (2.47 g, 23.3 mmol). The mixture was sparged with argon for 15 min and then heated at reflux for 18 h. The mixture was then absorbed onto silica gel and dried under reduced pressure. After dry loading, the product was purified by FCC (10-75% EtOAc/heptane) to give 3-cyclopropyl-N-((2,4-dimethoxy-6-vinylpyrimidin-5-yl)methyl)-1-ethyl-1H-pyrazol-5-amine. MS (ESI+) m/z 330.1 (M+H)+.

後処理

  1. customThe mixture was sparged with argon for 15 min
  2. temperatureheated
  3. temperatureat reflux for 18 h
  4. customThe mixture was then absorbed onto silica gel
  5. customdried under reduced pressure
  6. customAfter dry loading
  7. customthe product was purified by FCC (10-75% EtOAc/heptane)

出典と根拠

ORDレコード
ord-0c2d60243c7b4d8db4b4634857a6857c
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

関連ノート

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