Phosphorus oxychloride → 4-Chloro-2-(pyrazin-2-yl)-5-methyl-thieno-[2,3-d]-pyrimidine

Reaction equation

[C:1]([C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1)#[N:2].[NH2:9][C:10]1[S:11][CH:12]=[C:13]([CH3:20])[C:14]=1[C:15](OCC)=O.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:15]1[C:14]2[C:13]([CH3:20])=[CH:12][S:11][C:10]=2[N:9]=[C:1]([C:3]2[CH:8]=[N:7][CH:6]=[CH:5][N:4]=2)[N:2]=1

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 73172Pyrazinecarbonitrile

HCID 521132Ethyl 2-amino-4-methylthiophene-3-carboxylate

Product 1

HCID 184601144-Chloro-2-(pyrazin-2-yl)-5-methyl-thieno-[2,3-d]-pyrimidine

Procedure

With the procedure of Example 477, the reaction of 2-cyanopyrazine and 2-amino-4-methyl-3-ethoxycarbonyl-thiophene, and the subsequent reaction with POCl3 yields 4-chloro-2-(pyrazin-2-yl)-5-methyl-thieno-[2,3-d]-pyrimidine

Sources & evidence

ORD record: ord-d5565360238e43a89b4b1241b485bebd
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133271

Reaction notes

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