Sodium hydride → HCID 68181763, compound

HRID 1398637Notes

Reaction equation

HRID 1398637 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]([NH2:20])[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]([NH2:20])[CH:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2380124-Amino-6-chloropyrimidineHCID 129912416-iodo-1H-indazole

Product 1

HCID 68181763HCID 68181763, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-iodoindazole (500 mg, 2.05 mmol) in DMF (8 mL) was added NaH (60% oil dispersion, 131.12 mg, 3.28 mmol) at 0° C. The mixture was stirred at 0° C. to RT for 10 minutes before addition of 6-chloropyrimidin-4-amine (477.78 mg, 3.69 mmol) and stirring at 60° C. for 17 hr and then transferred to a pressure tube and heated at 70° C. for a further 6 hr. The reaction mixture was cooled and quenched by the addition of water (10 ml) and EtOAc (a few drops) was added. The resultant precipitate was collected by suction filtration and then thoroughly dried under high vacuum to give the title intermediate (248 mg): LC-MS: m/z=+338.20 (M+H)+.

Workup

  1. customtransferred to a pressure tube
  2. temperatureheated at 70° C. for a further 6 hr
  3. temperatureThe reaction mixture was cooled
  4. customquenched by the addition of water (10 ml) and EtOAc (a few drops)
  5. additionwas added
  6. filtrationThe resultant precipitate was collected by suction filtration
  7. customthoroughly dried under high vacuum

Sources & evidence

ORD record
ord-8abd5d306d2f495c8d0ad0770f8e0a96
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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