N,N-Dimethylaniline → 4-Chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine

HRID 2302665Notes

Reaction equation

HRID 2302665 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH3:6][C:7]1[S:15][C:10]2[N:11]=[CH:12][N:13]=[CH:14][C:9]=2[CH:8]=1.C[N:17]([CH3:24])[C:18]1[CH:23]=[CH:22][CH:21]=CC=1>>[Cl:3][C:14]1[C:9]2[CH:8]=[C:7]([CH3:6])[S:15][C:10]=2[N:11]=[C:12]([C:21]2[CH:24]=[N:17][CH:18]=[CH:23][CH:22]=2)[N:13]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 217930776-Methylthieno[2,3-d]pyrimidine

Product 1

HCID 184604134-Chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine

Procedure

The replacement of the keto group by Cl under the formation of the aromatic pyrimidine ring takes place under standard conditions. A mixture of POCl3 (18 ml) with 3,4-dihydro-4-oxo-2,4pyridin-3-yl)-6-methyl-thieno-[2,3-d]-pyrimidine (6 g) is refluxed for 4 hours under the addition of N,N-dimethylaniline (1,8 m). The usual workup yields 4-chloro-2-(pyridin-3-yl)-6-methyl-thieno-[2,3-d]-pyrimidine (5 g).

Sources & evidence

ORD record
ord-e06181e42c584c54bb8d23f96bb8385f
Source dataset
uspto-grants-2002_08
Patent number
US06432950B1

Reaction notes

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