Cl[C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:22][C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1.Cl.O1CCOCC1>CC(O)C.O1CCOCC1>[N:5]1[C:4]2[S:8][C:9]3[CH2:14][NH:13][CH2:12][CH2:11][C:10]=3[C:3]=2[C:2]([NH:22][C:23]2[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=2)=[N:7][CH:6]=1
tert-Butyl 4-chloro-5,8-dihydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine-7(6H)-carboxylate from Example 11A (1.00 g, 3.07 mmol) was dissolved in 2-propanol (10 mL). 3-Aminophenol (352 mg, 3.22 mmol) and a 4 M solution of gaseous hydrogen chloride in dioxane (38 μL, 0.15 mmol) were added, and the mixture was heated to 80° C. for 20 h. Subsequently, further 4 M hydrogen chloride in dioxane (1.54 mL, 6.14 mmol) was added, and the mixture was heated for additional 3 h. The precipitate was collected by suction filtration to yield 1.21 g of the title compound as hydrochloride salt. An analytical amount was dissolved in 1 M aqueous sodium hydroxide solution which was then concentrated in vacuo. The precipitate was collected by suction filtration and dried to yield the product as free base.
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