Acetic Acid → HCID 70484543, compound

HRID 1903311Notes

Reaction equation

HRID 1903311 reaction equation
[NH2:1][CH:2]1[N:7]=[C:6]2[N:8]=[CH:9][C:10]([CH2:11][NH2:12])=[C:5]2[C:4](=[O:13])[N:3]1[CH2:14][O:15][CH:16]([CH3:18])[CH3:17].[C:19]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20]1.[BH4-].[Na+].C(O)(=O)C>CO>[NH2:1][CH:2]1[N:7]=[C:6]2[N:8]=[CH:9][C:10]([CH2:11][NH:12][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:5]2[C:4](=[O:13])[N:3]1[CH2:14][O:15][CH:16]([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 4311764Sodium borohydrideHCID 70484286HCID 70484286, compound

Product 1

HCID 70484543HCID 70484543, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 10 ml of dry methanol were dissolved 251 mg of 2-amino-5-aminomethyl-3-isopropyloxymethylpyrrolo[2,3-d]pyrimidin-4-one and 252 mg of cyclopentanone and the mixture was allowed to stand under stirring at room temperature for 30 min. The mixture was then cooled to 0° C. and treated with 38 mg of sodium borohydride for 2 hrs. The excess reagent was decomposed with acetic acid, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to give 218 mg of 2-amino-5-cyclopentylaminomethyl-3-isopropyloxymethylpyrrolo[2,3-d]pyrimidin-4-one. The whole amount of this product was dissolved in 60 ml of 2 N--HCl and, after nitrogen purging, hydrolyzed at 70° C. for 5 hrs. The solvent was then evaporated to dryness under reduced pressure to give 196 mg of the desired compound.

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b05d7a23833540999e97e02ed72a01e3
Source dataset
uspto-grants-1984_03
Patent number
US04435569

Reaction notes

Loading…