CC[O-].[Na+].O=[C:6]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:14]([O:16]CC)=O.[NH2:19][C:20]([NH2:22])=[S:21].Cl>CCO>[SH:21][C:20]1[N:19]=[C:14]([OH:16])[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:6]=2[N:22]=1700 mg of NaOEt (10 mmol; 1.0 equiv) was added to 6 mL of abs. EtOH. To this solution was added, with stirring, 2 g of ethyl 2-keto-cyclooctylcarboxylate (10 mmol; 1.0 equiv) and 1 g of thiourea (13 mmol; 1.3 equiv). The mixture was refluxed for 6 hours. After cooling, the mixture was poured onto ice and acidified with hydrochloric acid. 1.33 g of 2-mercapto-5,6,7,8,9,10-hexahydrocycloocta[d]-pyrimidine-4-ol (63% yield) was obtained as a white solid.
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