Methyl chloroformate → HCID 14100205, compound

HRID 621488Notes

Reaction equation

HRID 621488 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][N:6]1[C:11]2[NH:12][N:13]=[C:14]([NH:15][CH3:16])[C:10]=2[C:9](=[O:17])[N:8]([CH2:18][CH2:19][CH3:20])[C:7]1=[O:21].C(N(CC)CC)C.Cl[C:33]([O:35][CH3:36])=[O:34]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][N:6]1[C:11]2=[N:12][N:13]([C:33]([O:35][CH3:36])=[O:34])[C:14]([NH:15][CH3:16])=[C:10]2[C:9](=[O:17])[N:8]([CH2:18][CH2:19][CH3:20])[C:7]1=[O:21]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 178456466HCID 178456466, compound

Product 1

HCID 14100205HCID 14100205, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 7-(3-chlorobenzyl)-3-methylamino-5-propylpyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (1.0 g, 2.9 mM) and triethylamine (1.2 ml, 8.6 mM) in dioxane (50 ml) was added dropwise methyl chloroformate (0.66 ml, 8.5 mM) at room temperature and the mixture was allowed to stir at the same temperature for 20 hours. The mixture was concentrated to dryness and the residue was triturated with water (10 ml). Recrystallization from chloroform/methanol gave colorless crystals (1.0 g, 86%), m.p. 164°-166° C.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue was triturated with water (10 ml)
  3. customRecrystallization from chloroform/methanol

Sources & evidence

ORD record
ord-5b2b75feba584b50b356de83fa857542
Source dataset
uspto-grants-1989_04
Patent number
US04824848

Reaction notes

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