Acetic Anhydride → HCID 88500510, compound

HRID 232036Notes

Reaction equation

HRID 232036 reaction equation
[NH2:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11]O)=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].[C:13]([O:16][C:17](=[O:19])[CH3:18])(=O)[CH3:14]>>[C:17]([O:16][CH2:13][CH2:14][N:9]1[C:3]2[N:4]=[CH:5][N:6]=[C:7]([Cl:8])[C:2]=2[N:1]=[C:10]1[CH3:11])(=[O:19])[CH3:18]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 2445272-((5-Amino-6-chloro-4-pyrimidinyl)amino)ethanol

Product 1

HCID 88500510HCID 88500510, compoundYield 21%

Procedure

2-(5-Amino-6-chloro-4-pyrimidinylamino)ethanol (Chem. Pharm. Bull., 1961, 9, 27) (5.71 g, 30.3 mmol) and acetic anhydride (50 ml) were heated together under nitrogen at 120° C. for 20 hours. The excess reagent was removed under reduced pressure and the residue was neutralised with aqueous sodium bicarbionate and extracted with dichloromethane (4×70 ml). The extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with ethyl acetate) to give 3-(2-acetoxyethyl)-2-methyl-7-chlorimidazo-[4,5-d]pyrimidine (1.597 g, 21%), as a white solid.

Workup

  1. customThe excess reagent was removed under reduced pressure
  2. extractionextracted with dichloromethane (4×70 ml)
  3. dry with materialThe extracts were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-5b6edcb8d9f94be6ab59bcf795b88446
Source dataset
uspto-grants-1989_07
Patent number
US04851412

Reaction notes

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