Orotic Acid → 2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl chloride

HRID 1671468Notes

Reaction equation

HRID 1671468 reaction equation
[C:1]([O:11]C)(=O)[C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=1.C(O)(=O)C1NC(=O)NC(=O)C=1.S(Cl)([Cl:26])=O>N1C=CC=CC=1>[C:1]([Cl:26])(=[O:11])[C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=1

Participants

5

Reactant 3

HCID 967Orotic AcidHCID 24386Thionyl ChlorideHCID 80257Orotic acid methyl ester

Product 1

HCID 204910432,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Org. Chem, 27, 3507 (1962) describes that methyl orotate can be synthesized by reacting orotic acid with thionyl chloride in the presence of a catalytic amount of pyridine to give orotyl chloride, which is then heated in methanol.

Workup

  1. customcan be synthesized

Sources & evidence

ORD record
ord-9bd61611db3047709e6cdaf9866f4a03
Source dataset
uspto-grants-2011_08
Patent number
US07994315B2

Reaction notes

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