Cesium carbonate → 2-chloro-5-methyl-N-(pyridin-3-yl)pyrimidin-4-amine

HRID 1170764

反応式

HRID 1170764 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:8][C:9]1[C:14]([CH3:15])=[CH:13][N:12]=[C:11]([Cl:16])[N:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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].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>[Cl:16][C:11]1[N:10]=[C:9]([NH:8][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[C:14]([CH3:15])=[CH:13][N:12]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 43021752-Chloro-5-methylpyrimidin-4-amine

生成物 1

HCID 575165052-chloro-5-methyl-N-(pyridin-3-yl)pyrimidin-4-amine収率 57.1%

試薬・触媒・溶媒 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 3-bromopyridine (379 mg, 2.4 mmol), 4-amino-2-chloro-5-methylpyrimidine (287 mg, 2.0 mmol), Pd2(dba)3 (18 mg, 0.02 mmol), xantphos (23 mg, 0.04 mmol) and cesium carbonate (975 mg, 3.0 mmol) in dioxane (15 mL) was heated under refluxed for 1 h under argon. The solvent was removed and the residue on purification by HPLC gave an intermediate, 2-chloro-5-methyl-N-(pyridin-3-yl)pyrimidin-4-amine as yellow solid (252 mg, 57%). For second Buckwald, a mixture of 2-chloro-5-methyl-N-(pyridin-3-yl)pyrimidin-4-amine (80 mg, 0.36 mmol), 4-(2-(pyrrolidin-1-yl)ethoxy)benzenamine (74 mg, 0.34 mmol), Pd2(dba)3 (3.2 mg, 0.003 mmol), xantphos (4.2 mg, 0.007 mmol) and cesium carbonate (234 mg, 0.72 mmol) in dioxane (5 mL) was heated under refluxed for 1 h under argon. The crude reaction mixture on purification using HPLC gave the title compound as light brown solid (28 mg, 20%).

後処理

  1. temperaturewas heated
  2. temperatureunder refluxed for 1 h under argon
  3. customThe solvent was removed
  4. customthe residue on purification by HPLC

出典と根拠

ORDレコード
ord-0234bbd9037243f9b9e22c69cba08d33
出典データセット
uspto-grants-2010_11
特許番号
US07825246B2

関連ノート

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