Sodium hydride → HCID 68181902, compound

HRID 1398635Notes

Reaction equation

HRID 1398635 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[C:14]1[N:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]2[C:22]([O:27][CH3:28])=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:15]=1>CN(C=O)C>[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[C:14]2[N:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]3[C:22]([O:27][CH3:28])=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 129912416-iodo-1H-indazoleHCID 86669604HCID 86669604, compound

Product 1

HCID 68181902HCID 68181902, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-iodo-1H-indazole (100 mg, 0.41 mmol) in DMF (5 mL) was added NaH (60% oil dispersion, 32.78 mg, 0.82 mmol)) at 0° C. The reaction mixture was stirred at 0° C. for 10 minutes before the addition of 6-chloro-N-(2-methoxypyridin-3-yl)pyrimidin-4-amine (126.7 mg, 0.55 mmol). The reaction mixture was then stirred at 110° C. for 18 hr. The reaction mixture was then cooled to RT, quenched by the addition of water (2 ml), EtOAc (a few drops) was added and the resultant precipitate was collected by suction filtration and thoroughly dried under high vacuum to give the title compound (120 mg, LC-MS: m/z=+444.90). This compound of 62% purity LC-MS (UV) was used without further purification.

Workup

  1. temperatureThe reaction mixture was then cooled to RT
  2. customquenched by the addition of water (2 ml), EtOAc (a few drops)
  3. additionwas added
  4. filtrationthe resultant precipitate was collected by suction filtration
  5. customthoroughly dried under high vacuum

Sources & evidence

ORD record
ord-0f6eb29c51b648f3b7670b728704486c
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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