Sodium Methoxide → HCID 178456476, compound

HRID 1086839Notes

Reaction equation

HRID 1086839 reaction equation
[NH2:1][C:2]1[N:3]([CH2:23][C:24](=O)[CH2:25][CH2:26][CH2:27]Cl)[N:4]=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH3:14])[C:7](=[O:15])[N:6]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[O-].[Na+]>CO>[CH2:16]([N:6]1[C:5]2=[N:4][N:3]3[CH:23]=[C:24]([CH:25]4[CH2:27][CH2:26]4)[NH:1][C:2]3=[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH3:14])[C:7]1=[O:15])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19818546HCID 19818546, compound

Product 1

HCID 178456476HCID 178456476, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-Amino-7-benzyl-2-(5-chloro-2-oxopentyl)-5-propylpyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (0.8 g) was suspended in methanol (20 ml). To the suspension was added a solution of 28% NaOMe in methanol (4 ml). The mixture was stirred at room temperature for 30 minutes and then at 60° C. for 3 hours. The reaction solution was concentrated to dryness. The residue was dissolved in methylene chloride, washed with water and concentrated to dryness to obtain crude crystals. Recrystallization from isopropyl ether gave colorless crystals (0.52 g), m.p. 264°-265° C.

Workup

  1. waitat 60° C. for 3 hours
  2. concentrationThe reaction solution was concentrated to dryness
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with water
  5. concentrationconcentrated to dryness
  6. customto obtain crude crystals
  7. customRecrystallization from isopropyl ether

Sources & evidence

ORD record
ord-efab78f3adc1442d8f7b609f989e3481
Source dataset
uspto-grants-1991_07
Patent number
US05032594

Reaction notes

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