Methanol → 3-(2-hydroxyethyl)-4H-pyrimido[2,1-a]isoquinolin-4-one

HRID 543288Notes

Reaction equation

HRID 543288 reaction equation
[C:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.CN([CH:15]=[C:16]1[CH2:20][CH2:19][O:18][C:17]1=[O:21])C.CO>C(OCC)(=O)C>[OH:18][CH2:19][CH2:20][C:16]1[C:17](=[O:21])[N:2]2[CH:3]=[CH:4][C:5]3[C:10]([C:1]2=[N:11][CH:15]=1)=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

5

Reactant 3

HCID 887MethanolHCID 737421-IsoquinolinamineHCID 3045663-Dimethylaminomethylenedihydrofuran-2-one

Product 1

HCID 138511033-(2-hydroxyethyl)-4H-pyrimido[2,1-a]isoquinolin-4-oneYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A heterogenous mixture containing 14.4 g of 1-isoquinolinamine (0.1 m) and 14.12 g of dihydro-3-[(dimethylamino)methylene]-2(3H)-furanone was heated to 200° C. for 4 hours to yield a homogenous yellow orange solution which solidified upon cooling to ambient temperature. The solidified reaction mixture was titurated with methanol and ethyl acetate to yield 3-(2-hydroxyethyl)-4H-pyrimido[2,1-a]isoquinolin-4-one as a tan solid (18.0 g; 75% yield) of the formula ##STR26## having a melting point of 185.2°-187.0° C. and the following elemental analysis:

Workup

  1. customto yield a homogenous yellow orange solution which
  2. temperatureupon cooling to ambient temperature
  3. customThe solidified reaction mixture

Sources & evidence

ORD record
ord-11ce99d2bcff44c49a98231153e41a2f
Source dataset
uspto-grants-1987_04
Patent number
US04661592

Reaction notes

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