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

HRID 491229

반응식

HRID 491229 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-791f3c64b07a45f48d9b42c795804a38
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528143B2

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