Sodium hydride → 4-{6-bromo-3-[(dimethylamino)methyl]-1H-indazol-1-yl}pyrimidin-2-amine

HRID 1398484Notes

Reaction equation

HRID 1398484 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][N:12]([CH3:14])[CH3:13])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[N:19]=1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][N:12]([CH3:14])[CH3:13])=[N:7][N:8]2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[N:19]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2233322-Amino-4-chloropyrimidineHCID 178483330HCID 178483330, compound

Product 1

HCID 681816554-{6-bromo-3-[(dimethylamino)methyl]-1H-indazol-1-yl}pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (6-Bromo-1H-indazol-3-ylmethyl)-dimethyl-amine (523 mg, 2.05 mmol) in DMF (8 mL) was added NaH (60% oil dispersion) (132 mg, 3.29 mmol) at 0° C. The reaction mixture was allowed to warm up to RT and was stirred for 15 min. A solution of 4-chloropyrimidin-2-amine (533 mg, 4.11 mmol) in DMF (3 mL) was added slowly. The resulting mixture was stirred at 60° C. for 18 hr. When the reaction mixture was partitioned between EtOAc (25 mL) and water (10 mL), precipitation occurred. The solid was collected by suction filtration and was washed with EtOAc to give the title compound: 1H NMR (500 MHz, DMSO) δ 2.22 (6H, s), 3.81 (2H, s), 7.04 (1H, d, J=5.52 Hz), 7.06-7.19 (2H, m), 7.50 (1H, m, J=8.51 Hz), 7.92 (1H, d, J=8.51 Hz), 8.27 (1H, d, J=5.52 Hz), 9.11 (1H, d, J=1.26 Hz); LC-MS: m/z=+348.9 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred at 60° C. for 18 hr
  2. customWhen the reaction mixture was partitioned between EtOAc (25 mL) and water (10 mL), precipitation
  3. filtrationThe solid was collected by suction filtration
  4. washwas washed with EtOAc

Sources & evidence

ORD record
ord-1a158154e398446fa451e9c43e14c132
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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