Acetic Anhydride → 3-(hydroxymethyl)-4H-pyrimido[2,1-a]isoquinolin-4-one acetate

HRID 543286Notes

Reaction equation

HRID 543286 reaction equation
[OH:1][CH2:2][C:3]1[C:16](=[O:17])[N:7]2[CH:8]=[CH:9][C:10]3[C:15]([C:6]2=[N:5][CH:4]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3.C(N(CC)CC)C.[C:25]([O:28]C(=O)C)(=[O:27])[CH3:26]>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[C:25]([OH:28])(=[O:27])[CH3:26].[OH:1][CH2:2][C:3]1[C:16](=[O:17])[N:7]2[CH:8]=[CH:9][C:10]3[C:15]([C:6]2=[N:5][CH:4]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 138510983-(hydroxymethyl)-4H-pyrimido[2,1-a]isoquinolin-4-one

Product 1

HCID 202061173-(hydroxymethyl)-4H-pyrimido[2,1-a]isoquinolin-4-one acetateYield 59%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To 3.0 g of 3-(hydroxymethyl)-4H-pyrimido [2,1-a]isoquinolin-4-one (13.3 mmole) suspended in 100 ml chloroform with 10 ml of triethylamine and a trace of 4-dimethylaminopyridine was added 5.0 g of acetic anhydride (50.0 mmole). The reaction mixture was refluxed for 2 hours, then cooled to room temperature and washed twice with water. The organic layer was dried and concentrated in vacuo to give a crude solid which was crystallized from methylene chloride/hexane to yield 3-(hydroxymethyl)-4H-pyrimido[2,1-a]isoquinolin-4-one acetate as yellow crystals (2.09 g, 59% yield) of the formula: ##STR22## having a melting point of 173.3° C. and the following elemental analysis:

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. washwashed twice with water
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customto give a crude solid which
  6. customwas crystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-0faf42f5766f4458b2bca0c140b558b9
Source dataset
uspto-grants-1987_04
Patent number
US04661592

Reaction notes

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