Sodium borohydride → HCID 68644536, compound

HRID 1158963Notes

Reaction equation

HRID 1158963 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[CH:33]=[CH:32][C:8]([CH2:9][O:10][C:11]2[C:20]3[CH2:19][O:18]C(=O)[N:16]([CH2:22][C:23]4[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=4)[C:15]=3[CH:14]=[N:13][C:12]=2[CH3:31])=[CH:7][CH:6]=1)#[N:4]>CO.ClCCl>[OH:18][CH2:19][C:20]1[C:11]([O:10][CH2:9][C:8]2[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:33][CH:32]=2)=[C:12]([CH3:31])[N:13]=[CH:14][C:15]=1[NH:16][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]#[N:28])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68644159HCID 68644159, compound

Product 1

HCID 68644536HCID 68644536, compoundYield 32.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (2.6 g, 69 mmol) was added to a solution of 4-[5-(4-cyano-benzyloxy)-6-methyl-2-oxo-4H-pyrido[3,4-d][1,3]oxazin-1 ylmethyl]-benzonitrile (83) (587 mg, 1.4 mmol) in a mixture of methyl alcohol and dichloromethane (1:1, 20 mL) at 0° C. The resulting solution was warmed to room temperature and stirred for 24 hours. The solvent was evaporated, residue was diluted with water and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated. The product was purified by column chromatography on silica gel using a gradient mixture of dichloromethane:methyl alcohol (1:0 to 40:1) as eluant to give 4-{[4-hydroxymethyl-6-methyl-5-(4-cyano-benzyloxy)-pyridin-3-ylamino]-methyl}-benzonitrile (87) (175 mg, 32% yield) as a colorless solid.

Workup

  1. customThe solvent was evaporated
  2. additionresidue was diluted with water
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was purified by column chromatography on silica gel using
  8. additiona gradient mixture of dichloromethane:methyl alcohol (1:0 to 40:1) as eluant

Sources & evidence

ORD record
ord-936578c9f72a4425b31725be22f6e9e1
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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