Sodium borohydride → HCID 68294558, compound

HRID 2279475Notes

Reaction equation

HRID 2279475 reaction equation
[CH:1]([NH:4][C:5]1[N:6]=[CH:7][C:8]2[C:14](=[O:15])[CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:9]=2[N:10]=1)([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[OH:15][CH:14]1[C:8]2[CH:7]=[N:6][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:10][C:9]=2[CH2:11][N:12]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:13]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68295370HCID 68295370, compound

Product 1

HCID 68294558HCID 68294558, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 126 (400 mg, 1.31 mmol) in MeOH (1 mL) cooled to 0° C. was added slowly NaBH4 (49.4 mg, 1.31 mmol) and the reaction was stirred at RT for 15 min. The reaction was quenched with water and the mixture was extracted with DCM. The organic layer was dried, filtered and concentrated to afford 400 mg (99%) of tert-butyl 5-hydroxy-2-(isopropylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (128) which was used with out additional purification.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with DCM
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8b5a313d56fa4006b34d6ab3a4a9e3d1
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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