Cl.[NH:2]1[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5][N:4]=[CH:3]1.S(Cl)([Cl:13])=O.C(OCC)C.[CH2:20](O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[ClH:13].[NH:4]1[CH2:5][CH:6]([C:8]([O:10][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:9])[CH2:7][N:2]=[CH:3]11,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride (1.0 g, 6.1 mmol) was suspended in dry benzyl alcohol (20 ml). To the mixture was added thionyl chloride (0.76 g, 6.39 mmol) and the resulting mixture was heated in an oil bath at 80° C. for 24 h. The clear solution was poured to anhydrous ethyl ether (100 ml) to induce precipitation. The white solids were collected and crystallized from methanol/THF to give 1.18 g (76%) of product (mp 113°-114° C.). 300 MHz nmr indicated the product. Microanalysis calc.: C 56.58, H 5.89, N 11.00; found: C 56.34, H 6.03, N 11.19.
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