Sodium hydride → 4-(6-iodo-1H-indazol-1-yl)-5-nitropyrimidin-2-amine

HRID 1398493Notes

Reaction equation

HRID 1398493 reaction equation
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH:14]1[NH:19][C:18]([NH2:20])=[N:17][CH:16]=[C:15]1[N+:21]([O-:23])=[O:22]>CN(C=O)C>[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[C:16]2[C:15]([N+:21]([O-:23])=[O:22])=[CH:14][N:19]=[C:18]([NH2:20])[N:17]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 129912416-iodo-1H-indazoleHCID 178508523HCID 178508523, compound2×

Product 1

HCID 681819814-(6-iodo-1H-indazol-1-yl)-5-nitropyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-iodo-1H-indazole (537 mg, 2.20 mmol) in DMF (16 mL) was added NaH (60% oil dispersion) (132 mg, 3.30 mmol) at 0° C. Mixture was stirred at RT for 10 min before addition of a portion of 6-chloro-5-nitro-1,6-dihydropyrimidin-2-amine (60% pure, 500 mg, 1.71 mmol). The mixture was stirred at RT for 20 min. Another portion of NaH (60% oil dispersion) (132 mg, 3.30 mmol) was added at RT. After 10 min, another portion of 6-chloro-5-nitro-1,6-dihydropyrimidin-2-amine (60% pure, 300 mg, 1.03 mmol) was added. Stirring continued for 30 min. The reaction mixture was cooled in an ice bath before quenching with water. The mixture was acidified by addition of 1 M aq HCl then the pH was adjusted to 8-9 by dropwise addition of saturated aq NaHCO3.

Workup

  1. waitAfter 10 min
  2. stirringStirring
  3. waitcontinued for 30 min
  4. temperatureThe reaction mixture was cooled in an ice bath
  5. custombefore quenching with water
  6. additionThe mixture was acidified by addition of 1 M aq HCl
  7. additionthe pH was adjusted to 8-9 by dropwise addition of saturated aq NaHCO3

Sources & evidence

ORD record
ord-076de23d22574060912e7c7e20b004e9
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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