Sodium Carbonate → 2-Amino-4-(4-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile

HRID 1356071

반응식

HRID 1356071 반응식
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1.[CH3:13][C:14]1[CH:15]=[C:16](B2OC3C=CC=CC=3O2)[O:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([C:16]2[O:17][CH:18]=[C:14]([CH3:13])[CH:15]=2)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 185072602-Amino-4-chloro-6-methylsulfanyl-pyrimidine-5-carbonitrileHCID 185075882-(4-Methyl-furan-2-yl)-benzo[1,3,2]dioxaborole

생성물 1

HCID 185074912-Amino-4-(4-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile수율 47%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 241Benzene용매

반응 조건

온도
90 °C

실험 절차

To a stirred suspension of 2.19 g (10.9 mmol) 2-amino-4-chloro-6-methylsulfanyl-pyrimidine-5-carbonitrile in 40 ml benzene at room temperature were added 2,40 g (12.0 mmol) 2-(4-methyl-furan-2-yl)-benzo[1,3,2]dioxaborole, 252mg (0.22 mmol) tetrakis(triphenylphosphine)palladium(O) and 11 ml (22.0 mmol) 2M aqueous sodium carbonate. The reaction mixture was heated at 90° C. for 16 h, then concentrated in vacuo. Chromatography (1/3 ethyl acetate/hexane then 1/1 ethyl acetate/hexane) afforded 1.26 g (47%) 2-amino-4-(4-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a light yellow crystalline solid. EI-MS m/e (%): 246 (M+, 61), 245 ([M—H]+, 100).

후처리

  1. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b629dd33f06e4fe5846ff2e1d6e33a8f
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586441B2

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