Sodium borohydride → HCID 68963721, compound

HRID 1396557Notes

Reaction equation

HRID 1396557 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:21])[N:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[CH:14]=[O:15])[C:5]2=[CH:4][N:3]=1.[BH4-].[Na+]>CO.C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:21])[N:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH2:14][OH:15])[CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[C:5]2=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86630405HCID 86630405, compound

Product 1

HCID 68963721HCID 68963721, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(6-Amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-4-methoxy-benzaldehyde (Example 75) (0.040 g, 0.141 mmol) is suspended in dry MeOH (2.5 ml) and THF (1 ml). The reaction mixture is cooled to 0-5° C. (ice-bath) and sodium borohydride (0.006 g, 0.1551 mmol) is cautiously added. The reaction mixture is stirred at room temperature for 24 hours, filtered, washing with MeOH and concentrated in vacuo. The resulting solid is triturated in MeOH (minimal) and collected by filtration to afford the title compound as an off-white solid.

Workup

  1. additionis cautiously added
  2. filtrationfiltered
  3. washwashing with MeOH
  4. concentrationconcentrated in vacuo
  5. customThe resulting solid is triturated in MeOH (minimal)
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a055e480179b4fc28d5714ff493c6383
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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