3-Cyanopyridine → 4-Chloro-2-(pyridin-3-yl)-6-nitro-thieno-[2,3-d]-pyrimidine

HRID 367770Notes

Reaction equation

HRID 367770 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:9][C:10]1[S:11][C:12]([N+:20]([O-:22])=[O:21])=[CH:13][C:14]=1[C:15](OCC)=O.O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:15]1[C:14]2[CH:13]=[C:12]([N+:20]([O-:22])=[O:21])[S:11][C:10]=2[N:9]=[C:1]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)[N:2]=1

Participants

4

Reactant 3

HCID 793-CyanopyridineHCID 24813Phosphorus oxychlorideHCID 27376083-Thiophenecarboxylic acid, 2-amino-5-nitro-, ethyl ester

Product 1

HCID 184599734-Chloro-2-(pyridin-3-yl)-6-nitro-thieno-[2,3-d]-pyrimidine

Procedure

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

Sources & evidence

ORD record
ord-6a43930355984acea27f83bf028078f6
Source dataset
uspto-grants-2000_10
Patent number
US06133271

Reaction notes

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