Sodium borohydride → HCID 68459993, compound

HRID 501202Notes

Reaction equation

HRID 501202 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:31][CH2:30][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[CH:27]=[CH:26][C:25]([CH:28]=[O:29])=[CH:24][CH:23]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4].[BH4-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:31][CH2:30][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58703310HCID 58703310, compound

Product 1

HCID 68459993HCID 68459993, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 102 (0.150 g, 0.36 mmol) in DCM was added NaBH4 (0.069 g, 1.81 mmol) under nitrogen atmosphere at 0° C. The reaction mixture temperature was raised to room temperature and continued stirring for 3 hr. The progress of the reaction was monitored by TLC and upon completion, the mixture was partitioned between DCM (25 mL) and water (15 mL) and the organic layer was separated, dried over Na2SO4 filtered and the solvent was removed under reduced pressure to give crude residue, which was purified by column chromatography using silica gel to provide methyl-2-{8-[4-(hydroxymethyl)phenyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (0.050 g, 33.2%).

Workup

  1. customthe mixture was partitioned between DCM (25 mL) and water (15 mL)
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customto give crude residue, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-90053e225edf4469877c5d825a01de2e
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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