Phosphorus oxychloride → Diethyl 2-chloropyrimidine-4,5-dicarboxylate

Reaction equation

O[C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][N:3]=1.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][N:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178469856HCID 178469856, compound

Product 1

HCID 21220647Diethyl 2-chloropyrimidine-4,5-dicarboxylateYield 30%

Procedure

The title compound was prepared as described in Example 7, but employing a solution of diethyl 2-hydroxypyrimidine-4,5-dicarboxylate (1.0 g, 4.2 mmol) and POCl3 (7.7 g, 50 mmol) resulting in a 30% yield (0.32 g); 1HNMR (CDCl3) δ 9.09 (d, 1H), 4.35 (m, 4H), 1.30 (m, 6H).

Workup

customresulting in a 30% yield (0.32 g)

Sources & evidence

ORD record: ord-3e8e0ebe845542ea81fad923af3d74c6
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05852028

Reaction notes

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