Phosphorus oxychloride → 4-Chloro-2-(isoxazol-5-yl)-6-chloro-thieno-[2,3-d]-pyrimidine

Reaction equation

[C:1]([C:3]1[O:7][N:6]=[CH:5][CH:4]=1)#[N:2].[NH2:8][C:9]1[S:10][C:11]([Cl:19])=[CH:12][C:13]=1[C:14](OCC)=O.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:14]1[C:13]2[CH:12]=[C:11]([Cl:19])[S:10][C:9]=2[N:8]=[C:1]([C:3]2[O:7][N:6]=[CH:5][CH:4]=2)[N:2]=1

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 112287641,2-Oxazole-5-carbonitrile

HCID 141699662-Amino-5-chloro-3-ethoxycarbonyl-thiophene

Product 1

HCID 184604324-Chloro-2-(isoxazol-5-yl)-6-chloro-thieno-[2,3-d]-pyrimidine

Procedure

With the procedure of Example 477, the reaction of 5-cyanoisoxazole and 2-amino-5-chloro-3-ethoxycarbonyl-thiophene, and the subsequent reaction with POCl3 yields 4-chloro-2-(isoxazol-5-yl)-6-chloro-thieno-[2,3-d]-pyrimidine

Sources & evidence

ORD record: ord-d5e4b1c1fbf141b5a0d15fef4695d08f
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133271

Reaction notes

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