N,N-Dimethylaniline → 4-(4-Chloro-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl)-benzoic acid methylester

HRID 617513Notes

Reaction equation

HRID 617513 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH3:6][O:7][C:8](=[O:26])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][C:17](=O)[C:18]3[CH:23]=[C:22]([CH3:24])[S:21][C:19]=3[N:20]=2)=[CH:11][CH:10]=1.CN(C)C1C=CC=CC=1>>[CH3:6][O:7][C:8](=[O:26])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[C:17]([Cl:3])[C:18]3[CH:23]=[C:22]([CH3:24])[S:21][C:19]=3[N:20]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 23289523Methyl 4-(3,4-dihydro-4-oxo-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl)-benzoate

Product 1

HCID 158405144-(4-Chloro-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl)-benzoic acid methylester

Procedure

A mixture of POCl3 (18 ml) with 4-(3,4-dihydro-4-oxo-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl)-benzoic acid methylester (6 g) is refluxed 4 hours under the addition of N,N-dimethylaniline (1.8 ml). The usual workup yields 4-(4-chloro-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl)-benzoic acid methylester (5 g).

Sources & evidence

ORD record
ord-f40b423258c64ac7898d6d1a41e43dcb
Source dataset
uspto-grants-1999_09
Patent number
US05948911

Reaction notes

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