Sodium hydride → 1-(2-aminopyrimidin-4-yl)-1H-indazole-6-carbonitrile

HRID 1398487Notes

Reaction equation

HRID 1398487 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=2)[CH:3]=[N:2]1.[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[N:16]=1>CN(C=O)C>[NH2:21][C:17]1[N:18]=[C:19]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=3)[CH:3]=[N:2]2)[CH:20]=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2233322-Amino-4-chloropyrimidineHCID 4225291H-indazole-6-carbonitrile

Product 1

HCID 601639071-(2-aminopyrimidin-4-yl)-1H-indazole-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-indazole-6-carbonitrile (200 mg, 1.40 mmol) in DMF (2 mL), was added NaH (60% oil dispersion) (89.4 mg, 2.24 mmol). The reaction mixture was stirred for 10 min at RT before addition of 4-chloropyrimidin-2-amine (362 mg, 2.79 mmol). The reaction mixture was stirred at RT for 1 hr then heated at 50° C. in a sealed tube for 18 hr. LC-MS (Method B) indicated a mixture of desired product and a regiosiomer by-product [21%, Retention time=1.65 min, m/z=237.4 (M+H)+] and [29%, Retention time=1.43 min, m/z=237.4 (M+H)+]. The reaction was quenched by addition of water (1 mL) and EtOAc (3 mL). The precipitated solid was collected by suction filtration: LC-MS (Method B): Retention time=1.65 min.

Workup

  1. temperaturethen heated at 50° C. in a sealed tube for 18 hr

Sources & evidence

ORD record
ord-a6ca847efc534e74a618ae8aff0e2181
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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