Sodium hydride → 4-(6-bromo-3-methyl-1H-indazol-1-yl)pyrimidin-2-amine

HRID 1398481Notes

Reaction equation

HRID 1398481 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:11])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[N:16]=1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:11])=[N:7][N:8]2[C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[N:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2233322-Amino-4-chloropyrimidineHCID 178434209HCID 178434209, compound

Product 1

HCID 681818654-(6-bromo-3-methyl-1H-indazol-1-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-3-methylindazole (300 mg, 1.42 mmol) in DMF (6 mL) was added NaH (60% oil suspension) (91 mg, 2.27 mmol) at 0° C. The mixture was stirred at RT for 10 min before addition of 4-chloropyrimidin-2-amine (368 mg, 2.84 mmol). Stirring continued at 60° C. for 2 hr. After standing at RT overnight the reaction mixture was quenched by addition of water (10 mL). The mixture was extracted with EtOAc (2×15 mL). During the process of extraction solid formed was removed by suction filtration. The organic layer was washed with water (2×5 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with EtOAc-heptane (1:1) to give the title intermediate as a white solid: 1H NMR (250 MHz, DMSO) δ 2.53-2.64 (3H, m), 6.69-7.21 (3H, m), 7.43-7.62 (1H, m), 7.76-7.89 (1H, m), 8.18-8.38 (1H, m), 8.92-9.15 (1H, m); LC-MS: m/z=+303.95/305.65 (M+H).

Workup

  1. waitAfter standing at RT overnight
  2. customthe reaction mixture was quenched by addition of water (10 mL)
  3. extractionThe mixture was extracted with EtOAc (2×15 mL)
  4. extractionDuring the process of extraction solid
  5. customformed
  6. customwas removed by suction filtration
  7. washThe organic layer was washed with water (2×5 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was triturated with EtOAc-heptane (1:1)

Sources & evidence

ORD record
ord-0ad4354b4f64472d82a75018a7321e6f
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

Loading…