Acetic Acid → HCID 12018226, compound

HRID 1280440Notes

Reaction equation

HRID 1280440 reaction equation
[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[N:15][CH:16]=[C:11]2[C:10]([C:17]2[O:18][C:19]([CH:22]=[O:23])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.C(O)(=O)C>C(O)CC>[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[N:15][CH:16]=[C:11]2[C:10]([C:17]2[O:18][C:19]([CH2:22][OH:23])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 15391112HCID 15391112, compound

Product 1

HCID 12018226HCID 12018226, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

0.6 g (1.97 mmol) of 1-benzyl-3-(5-formyl-2-furyl)pyrazolo[3,4-d]pyrimidine (Rf=0.65, SiO2, ethyl acetate) is treated with 60 mg of NaBH4 with good stirring in 20 ml of 1-propanol at room temperature. After 15 min, 50 ml of water and 2.5 ml of glacial acetic acid are added. After partially concentrating in a rotary evaporator, the mixture is extracted with ethyl acetate, and the extract is dried and concentrated in a rotary evaporator after addition of toluene. After chromatography on SiO2, 74.8 mg (12.4% of theory) of product are obtained (m.p. 165° C., Rf=0.43, SiO2, ethyl acetate).

Workup

  1. concentrationAfter partially concentrating in a rotary evaporator
  2. extractionthe mixture is extracted with ethyl acetate
  3. customthe extract is dried
  4. concentrationconcentrated in a rotary evaporator
  5. additionafter addition of toluene
  6. customAfter chromatography on SiO2, 74.8 mg (12.4% of theory) of product are obtained (m.p. 165° C., Rf=0.43, SiO2, ethyl acetate)

Sources & evidence

ORD record
ord-35757c131ecd49d9adeda8ff98c96303
Source dataset
uspto-grants-2002_09
Patent number
US06451805B1

Reaction notes

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