Phosphorus oxychloride → 5-Methylthieno[2,3-d]pyrimidine

Reaction equation

[C:1](C1ON=CC=1)#[N:2].[NH2:8][C:9]1[S:10][CH:11]=[C:12]([CH3:19])[C:13]=1[C:14](OCC)=O.O=P(Cl)(Cl)Cl>>[CH3:19][C:12]1[C:13]2[CH:14]=[N:2][CH:1]=[N:8][C:9]=2[S:10][CH:11]=1

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

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

HCID 112287641,2-Oxazole-5-carbonitrile

Product 1

HCID 122857285-Methylthieno[2,3-d]pyrimidine

Procedure

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

Sources & evidence

ORD record: ord-0f92715da2aa454a9ac089292160ef3e
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06432950B1

Reaction notes

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