Sodium borohydride → HCID 58548308, compound

HRID 467734Notes

Reaction equation

HRID 467734 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[C:15]([NH:16][C:17]3[CH:18]=[N:19][CH:20]=[N:21][CH:22]=3)=[N:14][CH:13]=[C:12]([C:23](=[O:25])[CH3:24])[N:11]=2)=[O:9])[C:4]([C:26](=[O:29])[NH:27][CH3:28])=[N:3]1.[BH4-].[Na+]>C(O)C>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[C:15]([NH:16][C:17]3[CH:22]=[N:21][CH:20]=[N:19][CH:18]=3)=[N:14][CH:13]=[C:12]([CH:23]([OH:25])[CH3:24])[N:11]=2)=[O:9])[C:4]([C:26](=[O:29])[NH:27][CH3:28])=[N:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86660191HCID 86660191, compound

Product 1

HCID 58548308HCID 58548308, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred, cooled (0° C.) suspension of 6-acetyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carboxylic acid (1-methyl-3-methylcarbamoyl-1H-pyrazol-4-yl)-amide (12 mg, 30.4 μmol) in ethanol (2 ml) under an argon atmosphere was added sodium borohydride (1.15 mg, 30.4 μmol) in one portion. Stirring was continued for 1 hr at rt. More sodium borohydride (3 eq.) was added in one portion. The mixture was heated to reflux and stirring as continued for 30 min. The reaction was cooled to rt and concentrated. The crude product was purified by silica gel chromatography using a CH2Cl2/MeOH gradient as eluent. The title compound (4 mg, 33%) as yellow solid.

Workup

  1. temperatureTo a stirred, cooled
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. stirringstirring
  5. waitas continued for 30 min
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e00ebfb9982d45539402b93c0a8ac355
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

Loading…