Phosphorus oxychloride → HCID 15620865, compound

HRID 1163861Notes

Reaction equation

HRID 1163861 reaction equation
C(O[C:4]([C:6]1[C:10]([CH3:11])=[C:9]([CH3:12])S[C:7]=1[NH2:13])=[O:5])C.CO[C:16]1[NH:17][CH2:18][CH2:19][CH:20]=1.P(Cl)(Cl)(Cl)=O>[Ni]>[CH3:11][CH:10]([C:6]1[C:4](=[O:5])[N:17]2[CH2:18][CH2:19][CH2:20][C:16]2=[N:13][CH:7]=1)[CH2:9][CH3:12]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 78536Ethyl 2-amino-4,5-dimethyl3-thenoateHCID 127618282-Methoxypyrroline

Product 1

HCID 15620865HCID 15620865, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

According to Khim. Geterosikl. Soedin. 6, 765, 1975 ethyl-2-amino-4,5-dimethyl-thiophene-3-carboxylate is reacted with 2-methoxy-pyrroline in the presence of phosphoryl chloride and the obtained 2,3-dimethyl-4-oxo-5,6-tetramethylene-4H thieno[2,3-d]pyrimidine is desulphurated in an alcoholic solution wih Raney-nickel and thus 3-(1-methyl-propyl)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine is obtained. In the complicated two-step synthesis the pyrrolo-pyrimidine derivative is obtained with a yield of 36.5%.

Sources & evidence

ORD record
ord-9c2196c3a13b4f84942155b6625fcdf5
Source dataset
uspto-grants-1983_01
Patent number
US04367229

Reaction notes

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