Benzylamine → HCID 178448670, compound

HRID 621494Notes

Reaction equation

HRID 621494 reaction equation
[CH2:1]([N:5]1[C:10](=[O:11])[C:9]2[C:12]([NH:15][CH3:16])=[N:13][NH:14][C:8]=2[N:7]([CH2:17][CH2:18]Cl)[C:6]1=[O:20])[CH2:2][CH2:3][CH3:4].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1.Cl>[CH2:1]([N:5]1[C:10](=[O:11])[C:9]2[C:12]([NH:15][CH3:16])=[N:13][NH:14][C:8]=2[N:7]([CH2:17][CH2:18][NH:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:6]1=[O:20])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 178448669HCID 178448669, compound

Product 1

HCID 178448670HCID 178448670, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-butyl-7-(2-chloroethyl)-3-methylaminopyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (0.6 g, 2 mM) and benzylamine (0.66 ml, 6 mM) in dioxane (20 ml) was refluxed for 20 hours. The reaction solution was concentrated to dryness under reduced pressure to give a syrup, which was poured onto ice-water to give colorless crystals. The crystls were dissolved in 1N-HCl and insoluble material was filtered off, followed by addition of 1N-ammonia water to give crystals. Recrystallization from DMF/methanol/water afforded colorless needles (0.32 g, 43%), m.p. 198°-200° C.

Workup

  1. temperaturewas refluxed for 20 hours
  2. concentrationThe reaction solution was concentrated to dryness under reduced pressure
  3. customto give a syrup, which
  4. additionwas poured onto ice-water
  5. customto give colorless crystals
  6. filtrationwas filtered off
  7. additionfollowed by addition of 1N-ammonia water
  8. customto give crystals
  9. customRecrystallization from DMF/methanol/water afforded colorless needles (0.32 g, 43%), m.p. 198°-200° C.

Sources & evidence

ORD record
ord-4734e616ceaf4cbdbc67ac9c89544a68
Source dataset
uspto-grants-1989_04
Patent number
US04824848

Reaction notes

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