Cesium carbonate → Methyl 4-methyl-3-(4-phenylpyrimidin-2-ylamino)benzoate

HRID 383873

反応式

HRID 383873 の反応式
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:18]([O:20][CH3:21])=[O:19].C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:25][C:24]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[NH:13][C:9]1[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:12]=[CH:11][N:10]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 5987772-Amino-4-phenylpyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7015747Methyl 3-bromo-4-methylbenzoate

生成物 1

HCID 68466271Methyl 4-methyl-3-(4-phenylpyrimidin-2-ylamino)benzoate収率 52.2%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

A mixture of 4-phenylpyrimidin-2-amine (100 mg, 0.58 mmol) and methyl 3-bromo-4-methylbenzoate (111 mg, 0.48 mmol), Cs2CO3 (221 mg, 0.68 mmol), Pd2(dba)3 (22 mg, 0.024 mmol) and Xantphos (22 mg, 0.039 mmol) in a microwave reaction vessel was suspended in 5 mL of toluene. The reaction mixture was heated in a microwave at 130° C. for 30 min, and then at 180° C. for 30 min. After cooling, the mixture was purified by ISCO system to give 80 mg of product (yield: 43%). MS (ESI+) m/z 320.1 [M+H]+.

後処理

  1. customin a microwave reaction vessel
  2. temperatureAfter cooling
  3. customthe mixture was purified by ISCO system

出典と根拠

ORDレコード
ord-f292fd24b2054d5c854f4ca62260dc6d
出典データセット
uspto-grants-2013_02
特許番号
US08367686B2

関連ノート

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