Sodium borohydride → HCID 178470043, compound

HRID 1093067Notes

Reaction equation

HRID 1093067 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:19]2[NH:20][C:21](=O)[C:22]([OH:30])=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:24]=2)[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:19]2[NH:20][CH2:21][C:22]([OH:30])=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:24]=2)[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 136061310HCID 136061310, compound

Product 1

HCID 178470043HCID 178470043, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(1-(benzyloxycarbonylamino)-4-oxocyclohexyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (1.5 g, 3.5 mmol) in methanol (35 mL) at room temperature was added NaBH4 (138 mg, 3.66 mol) and the resulting mixture was stirred for 1 h. Methanol was then removed under reduced pressure and the mixture was diluted with CH2Cl2 (200 mL), washed with 1N HCl (100 mL) followed by brine (100 mL). The organic fraction was dried (Na2SO4), filtered and concentrated to afford the title compound as a light yellow solid (1.3 g, 86% yield). 1H NMR (500 MHz, DMSO-D6) δ: 12.46 (s, 1H), 10.24 (s, 1H), 7.31-7.35 (m, 5H), 7.11 (brs, 1H), 4.28-4.32 (m, 2H), 4.29 (q, 2H, J=7.22 Hz), 3.43-3.46 (m, 1H), 2.31-2.33 (m, 1H), 2.15-2.22 (m, 2H), 1.77-1.83 (m, 2H), 1.65-1.67 (m, 2H), 1.44-1.49 (m, 2H), 1.28 (t, 3H, J=7.22 Hz). LCMS (M+H)=432.37.

Workup

  1. customMethanol was then removed under reduced pressure
  2. additionthe mixture was diluted with CH2Cl2 (200 mL)
  3. washwashed with 1N HCl (100 mL)
  4. dry with materialThe organic fraction was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-be1ec07902b44da6b42161651ff1d67d
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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