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

HRID 367776Notes

Reaction equation

HRID 367776 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]([N+:19]([O-:21])=[O:20])=[CH:12][C:13]=1[C:14](OCC)=O.O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:14]1[C:13]2[CH:12]=[C:11]([N+:19]([O-:21])=[O:20])[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

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 27376083-Thiophenecarboxylic acid, 2-amino-5-nitro-, ethyl esterHCID 112287641,2-Oxazole-5-carbonitrile

Product 1

HCID 184600844-Chloro-2-(isoxazol-5-yl)-6-nitro-thieno-[2,3-d]-pyrimidine

Procedure

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

Sources & evidence

ORD record
ord-907e089fca9846559f9af968fdce24a7
Source dataset
uspto-grants-2000_10
Patent number
US06133271

Reaction notes

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