Acetic Acid → HCID 70483911, compound

HRID 1903310Notes

Reaction equation

HRID 1903310 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].[CH:19](=O)[CH2:20][CH3:21].[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][CH2:19][CH2:20][CH3:21])=[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 527PropanalHCID 4311764Sodium borohydrideHCID 70484286HCID 70484286, compound

Product 1

HCID 70483911HCID 70483911, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 5.0 ml of dry methanol were dissolved 251 mg of 2-amino-5-aminomethyl-3-isopropyloxymethylpyrrolo[2,3-d]pyrimidin-4-one and 64 mg of propionaldehyde and the solution was allowed to stand under stirring at room temperature for 30 min. Then, 20 mg of sodium borohydride was added and the mixture was reacted at room temperature for an hour. The excess reagent was decomposed with a small amount of acetic acid, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to give 76 mg of 2-amino-5-propylaminomethyl-3-isopropyloxymethylpyrrolo[2,3-d]pyrimidin-4-one. The whole amount of this product was dissolved in 30 ml of 2 N--HCl and, after nitrogen purging, hydrolyzed under heating at 70° C. for 6.5 hours. The solvent was then evaporated off under reduced pressure to give 73 mg of the desired compound.

Workup

  1. customthe mixture was reacted at room temperature for an hour
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0c3bb4d62ac0464db36ef4a3af5122f3
Source dataset
uspto-grants-1984_03
Patent number
US04435569

Reaction notes

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