Sodium cyanoborohydride → HCID 19804696, compound

HRID 1682133Notes

Reaction equation

HRID 1682133 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]=[CH:13][CH:14]([CH3:16])[CH3:15])[N:3]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:9][CH2:10]2)[N:5]=[C:4]([N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])[N:3]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 54385574HCID 54385574, compound

Product 1

HCID 19804696HCID 19804696, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

8.55 g (0.029 mol) of N-(4-methyl-6-cyclopropylpyrimidin-2-yl)-N-phenylisobutyraldehyde hydrazone are dissolved in 30 ml of methanol and 2 ml of glacial acetic acid. 2.14 g (0.029 mol) of sodium cyanoborohydride are then added in portions with stirring. The reaction proceeds exothermically; the temperature is maintained at 10°-15° C. by cooling. After 1 hour, the batch is worked up by extraction with ethyl acetate and water and the organic phase is concentrated using a rotary evaporator to give 8.5 g of crude product. Purification by column chromatography on silica gel (eluant: 85% hexane/15% ethyl acetate) affords 7.6 g (89% of the theoretical yield) of the title compound in the form of an oil having a refractive index of [n]D25 =1.5733.

Workup

  1. temperaturethe temperature is maintained at 10°-15° C.
  2. temperatureby cooling
  3. extractionthe batch is worked up by extraction with ethyl acetate and water
  4. concentrationthe organic phase is concentrated
  5. customa rotary evaporator
  6. customto give 8.5 g of crude product
  7. customPurification by column chromatography on silica gel (eluant: 85% hexane/15% ethyl acetate)
  8. customaffords 7.6 g (89% of the

Sources & evidence

ORD record
ord-6d50ba8e751c426bbb5a607288d73084
Source dataset
uspto-grants-1992_12
Patent number
US05175293

Reaction notes

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