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

HRID 1912210

반응식

HRID 1912210 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-c31a7e7cd6a44cc59355be8468bc890f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604042B2

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