Sodium borohydride → HCID 25213707, compound

HRID 2194794Notes

Reaction equation

HRID 2194794 reaction equation
[CH2:1]([N:3]1[C:8]([C:9]([C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([CH3:19])[CH:18]=2)[C:14]#[N:15])=[O:10])=[C:7]([CH:20]([CH3:22])[CH3:21])[C:6](=[O:23])[NH:5][C:4]1=[O:24])[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([N:3]1[C:8]([CH:9]([OH:10])[C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([CH3:19])[CH:18]=2)[C:14]#[N:15])=[C:7]([CH:20]([CH3:21])[CH3:22])[C:6](=[O:23])[NH:5][C:4]1=[O:24])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride3×HCID 25215428Ainuovirine

Product 1

HCID 25213707HCID 25213707, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(3-ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (3) (0.700 g, 2.15 mmol) in ethanol (61 mL) at 0° C. was added sodium borohydride (0.081 g, 2.15 mmol) and the reaction mixture was stirred at 0° C. for 2 h, then at room temperature overnight. More sodium borohydride (0.081 g, 2.15 mmol). was then added, and the mixture was stirred for 24 h. More sodium borohydride (0.081 g, 2.15 mmol) was again added, and stirring was continued for 6 h. The reaction mixture was concentrated and quenched with saturated NH4Cl solution, acidified with 1N HCl and then extracted with ethyl acetate (2×). The combined organic layer dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 30 to 60% ethyl acetate/hexane) to give impure product. The impure product was purified again by flash column chromatography (silica gel, 0 to 5% methanol/dichloromethane), followed by purified by flash column chromatography (silica gel, 40 to 60% ethyl acetate/hexane) to give a white solid (0.31 g, 44%). 1H NMR (300 MHz, CD3OD): 7.55 (s, 1H), 7.47 (s, 1H), 7.43 (s, 1 H), 6.18 (s, 1H), 3.73 (q, J=6.9 Hz, 2H), 3.12-3.07 (m, 1H), 2.37 (s, 3H), 1.30 (d, J=7.2 Hz, 3H), 1.11 (d, J=6.6 Hz, 3H), 0.92-0.84 (m, 3H); Mass Spectrum: 328.1 (M+H).

Workup

  1. customat room temperature
  2. customovernight
  3. additionwas then added
  4. stirringthe mixture was stirred for 24 h
  5. stirringstirring
  6. waitwas continued for 6 h
  7. concentrationThe reaction mixture was concentrated
  8. customquenched with saturated NH4Cl solution
  9. extractionextracted with ethyl acetate (2×)
  10. dry with materialThe combined organic layer dried (MgSO4)
  11. concentrationconcentrated
  12. custompurified by flash column chromatography (silica gel, 30 to 60% ethyl acetate/hexane)
  13. customto give impure product
  14. customThe impure product was purified again by flash column chromatography (silica gel, 0 to 5% methanol/dichloromethane)
  15. customby purified by flash column chromatography (silica gel, 40 to 60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-852b7e2b45dd48afabf0dfbc6a91d4e6
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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