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

HRID 1398494Notes

Reaction equation

HRID 1398494 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-1ae29d298f844cc2b73c8113f1d4e13e
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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