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

HRID 1398494ノート

反応式

HRID 1398494 の反応式
[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

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 681819814-(6-iodo-1H-indazol-1-yl)-5-nitropyrimidin-2-amine2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-1ae29d298f844cc2b73c8113f1d4e13e
出典データセット
uspto-grants-2014_12
特許番号
US08901313B2

反応ノート

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