Formamide → 4-Chloro-6-(methylthio)thieno[3,2-d]pyrimidine

HRID 2408944Notes

Reaction equation

HRID 2408944 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([S:7][CH3:8])[S:4][C:3]=1[C:9](OCC)=O.[CH:14]([NH2:16])=O.P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:9]1[C:3]2[S:4][C:5]([S:7][CH3:8])=[CH:6][C:2]=2[N:1]=[CH:14][N:16]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 24813Phosphorus oxychlorideHCID 69671703HCID 69671703, compound

Product 1

HCID 594244514-Chloro-6-(methylthio)thieno[3,2-d]pyrimidine

Procedure

As shown in scheme I, cyclisation of ethyl 3-amino-5-(methylthio)-thiophene-2-carboxylate using formamide and further treatment with phosphorous oxychloride gave 4-chloro-6-(methylthio)thieno[3,2-d]pyrimidine in good yield. Treatment of this 4-chlorocompound with 3-amino-5-tert-butylselenophene-2-carboxamide in the presence of DMF/NaOH gave 3-(6-(methylthio)thieno[3,2-d]pyrimidin-4-ylamino)-5-tert-butylselenophene-2-carboxamide.

Sources & evidence

ORD record
ord-05089311e182435a8ecdb5c86edb3b1c
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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