Reaction SMILES: C([O:9][CH2:10][CH2:11][N:12]1[CH:38]=[C:15]2[CH2:16][N:17]([C:20]3[C:21]4[S:37][CH:36]=[CH:35][C:22]=4[N:23]=[C:24]([C:26]4[CH:31]=[C:30]([F:32])[C:29]([Cl:33])=[CH:28][C:27]=4[F:34])[N:25]=3)[CH2:18][CH2:19][C:14]2=[N:13]1)(=O)C1C=CC=CC=1.[OH-].[Na+].Cl>C1COCC1.CCO>[ClH:33].[Cl:33][C:29]1[C:30]([F:32])=[CH:31][C:26]([C:24]2[N:25]=[C:20]([N:17]3[CH2:18][CH2:19][C:14]4=[N:13][N:12]([CH2:11][CH2:10][OH:9])[CH:38]=[C:15]4[CH2:16]3)[C:21]3[S:37][CH:36]=[CH:35][C:22]=3[N:23]=2)=[C:27]([F:34])[CH:28]=1
Reactant: O=C(OCCn1cc2c(n1)CCN(c1nc(-c3cc(F)c(Cl)cc3F)nc3ccsc13)C2)c1ccccc1
Agent: Cl
Agent: [Na+]
Agent: [OH-]
Solvent: CCO
Solvent: C1CCOC1
Product: OCCn1cc2c(n1)CCN(c1nc(-c3cc(F)c(Cl)cc3F)nc3ccsc13)C2
Temperature: 60 °C
Reaction time: 1 h
Yield: 218.7 %

Procedure:
A mixture of 1.41 g of 4-chloro-2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine, 1.28 g of a mixture of 2-(4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-yl)ethanol and 2-(4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-2-yl)ethanol, 3.87 ml of diisopropyl ethylamine and 30 ml of acetonitrile was stirred for 12 hours at 80° C. After 100 ml of water was added to the reaction mixture and extracted with EtOAc, the organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-MeOH) and 1.19 g of a foam-like substance was obtained. A mixture of the obtained foam-like substances 10 ml of pyridine and 0.62 ml of benzoyl chloride was stirred for one hour at room temperature. After 50 ml of water was added to the reaction mixture and extracted with EtOAc-THF mixed solvents the organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was recrystallized from EtOAc and the mother liquid was repeated recrystallization from EtOAc to give 716 mg of 2-{5-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-2-yl}ethyl benzoate was obtained. Further, this recrystallized mother liquid washed with ether-hexane mixed solvent and the washed liquid was concentrated under reduced pressure to give 636 mg of 2-{5-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-yl}ethyl benzoate. 716 mg of the obtained 2-{5-[2-(4-chloro-2,5-difluorophenyl)thieno-[3,2-d]pyrimidine-4-yl]-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-2-yl}ethyl benzoate was dissolved in 10 ml of THF-EtOH (2:1) solution and was added to 2.60 ml of 1M NaOH aq. The resultant was stirred for one hour at 60° C. and was left to cool to room temperature. Then, 30 ml of 1M HCl aq was added and washed with ether, the aqueous layer was made alkaline with 100 ml of 1M NaOH aq. After this was extracted with EtOAc, the organic layer was dried over anhydrous magnesium sulfate and the solution was removed under reduced pressure. The obtained residue was dissolved in 20 ml of THF and 10 ml of MeOH, and was added to 3 ml of 4M HCl-dioxane solution, concentrated under reduced pressure and a solid was obtained. This solid was recrystallized from EtOH-EtOAc to give 687 mg of 2-{5-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-2-yl}ethanol hydrochloride. Furthermore, the above-mentioned operation was carried out on the 636 mg of 2-{5-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-yl}ethyl benzoate to give 180 mg of 2-{5-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-yl}ethanol hydrochloride.