Lithium borohydride → HCID 131736981, compound

HRID 58184Notes

Reaction equation

HRID 58184 reaction equation
[BH4-].[Li+].[C:3]([O:7][C:8]([N:10]([C:24]1[CH:29]=[C:28]([N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH3:31])[N:27]=[CH:26][N:25]=1)[C:11]1[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1>[C:3]([O:7][C:8]([N:10]([C:11]1[CH:20]=[CH:19][C:14]([CH2:15][OH:16])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])[C:24]1[N:25]=[CH:26][N:27]=[C:28]([N:30]([CH3:31])[C:32](=[O:33])[O:34][C:35]([CH3:37])([CH3:38])[CH3:36])[CH:29]=1)=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 121317868HCID 121317868, compound

Product 1

HCID 131736981HCID 131736981, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (0.157 g, 7.14 mmol) was added to a solution of methyl 4-((tert-butoxycarbonyl)(6-((tert-butoxycarbonyl)(methyl)amino)pyrimidin-4-yl)amino)-3-nitrobenzoate (1.8 g, 3.57 mmol) in THF (20 mL) under an argon atmosphere at 0° C. The resulting mixture was then allowed to warm to rt and stirred for 12 h. The reaction mixture was then quenched with ice-water and diluted with ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate (3×40 mL). The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated to get a crude residue. The residue was purified by silica gel column chromatography to afford desired intermediate-6 (1.2 g, 75%) as a solid. MS (ESI): 476.1 [M+H]+.

Workup

  1. customThe reaction mixture was then quenched with ice-water
  2. additiondiluted with ethyl acetate
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (3×40 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b72c9a2114814d40818788dd7c037f60
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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