Reaction #3973

ord-6a823073ab7c4f51901f88aec89eb947

Reaction equation

CC(=O)O
acetic acid
COc1cc(C(=O)O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1
8-(2-methoxy-4-carboxy-phenyl)-1H,-3H-purin-2,6-dione
N
ammonia
O
water
→
COc1cc(C(N)=O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1
8-(2-Methoxy-4-aminocarbonyl-phenyl)-1H,3H-purin-2,6-dione

Reactants

CC(=O)O
acetic acid
COc1cc(C(=O)O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1
8-(2-methoxy-4-carboxy-phenyl)-1H,-3H-purin-2,6-dione
N
ammonia
O
water

Reagents

CN(C)C=O
dimethylformamide

Solvents

CN(C)C=O
dimethylformamide
O=S(Cl)Cl
thionyl chloride
O=S(Cl)Cl
thionyl chloride
CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe product precipitated
  2. 2
    Filtrationis filtered off

Procedure

A quantity of 2.3 gm of 8-(2-methoxy-4-carboxy-phenyl)-1H,-3H-purin-2,6-dione are refluxed for one hour in 50 ml of thionyl chloride with the addition of 1 drop of dimethylformamide. The excess thionyl chloride is drawn off, and the residue is stirred for 16 hours at ambient temperature with a solution of ammonia in dimethylformamide. The dimethylformamide is drawn off, the remainder is mixed with water and acidified with glacial acetic acid, and the product precipitated is filtered off.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04722929uspto-grants-1988_02