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

HRID 367766

Reaction equation

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

Participants

Reactant 3

HCID 949N,N-Dimethylaniline

HCID 24813Phosphorus oxychloride

HCID 232879063,4-Dihydro-4-oxo-2-(pyridin-3-yl)-6-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-(pyridin-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-77c8e4ca16474d61a764482e99ff9dde
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133271

Linked notes

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