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

HRID 366373Notes

Reaction equation

HRID 366373 reaction equation
O=P(Cl)(Cl)[Cl:3].O=[C:7]1[NH:12][C:11]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[N:10][C:9]2[S:23][C:24]([CH3:26])=[CH:25][C:8]1=2.CN(C)C1C=CC=CC=1>>[Cl:3][C:7]1[C:8]2[CH:25]=[C:24]([CH3:26])[S:23][C:9]=2[N:10]=[C:11]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[N:12]=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 18 ml of POCl3 with 6 g of methyl 4-(3,4-dihydro-4-oxo-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl)-benzoate is boiled for 4 hours with the addition of 1.8 ml of N,N-dimethylaniline. Customary working up gives 5 g of methyl 4-(4-chloro-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl)-benzoate.

Sources & evidence

ORD record
ord-c916f40f76f14264bf5761b9ed51f53e
Source dataset
uspto-grants-2000_10
Patent number
US06130223

Reaction notes

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