Dimethylformamide → 4-(6-iodo-1H-indazol-1-yl)pyrimidine-2,5-diamine

HRID 1398494노트

반응식

HRID 1398494 반응식
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[C:11]2[C:16]([N+:17]([O-])=O)=[CH:15][N:14]=[C:13]([NH2:20])[N:12]=2)=[CH:4][CH:3]=1.CN(C=O)C.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>CO.O>[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[C:11]2[C:16]([NH2:17])=[CH:15][N:14]=[C:13]([NH2:20])[N:12]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 681819814-(6-iodo-1H-indazol-1-yl)-5-nitropyrimidin-2-amine2회

생성물 1

HCID 681817304-(6-iodo-1H-indazol-1-yl)pyrimidine-2,5-diamine수율 11%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a suspension of 4-(6-iodo-1H-indazol-1-yl)-5-nitropyrimidin-2-amine (200 mg, 45% purity, 0.236 mmol) in a mixture of methanol (4 mL), DMF (3 mL) and water (3 mL) was added sodium dithionite (205 mg, 1.178 mmol) and sodium bicarbonate (99 mg, 1.178 mmol). The suspension was stirred at RT for 2 hr. After 2 hr LC-MS (Method B) showed 11% of desired product, 15% of starting 4-(6-iodo-1H-indazol-1-yl)-5-nitropyrimidin-2-amine (16-a) and 67% of degraded by-product. The reaction mixture was diluted with EtOAc (30 mL) and washed with water (2×10 mL), then dried over Na2SO4, filtered and concentrated in vacuo to give the crude title compound; m/z=+352.9 (M+H)+, (purity=11%). This intermediate was used in the next step without further purification.

후처리

  1. waitAfter 2 hr LC-MS (Method B) showed

출처 및 근거

ORD 기록
ord-1ae29d298f844cc2b73c8113f1d4e13e
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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