Sodium Hydroxide → 3,4,5,6,7,8-Hexahydro-3-[2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl]pyrido[4',3'; 4,5]thieno[2,3-d]pyrimidin-4-one

HRID 325081Notes

Reaction equation

C([N:4]1[CH2:33][CH2:32][C:7]2[C:8]3[C:13](=[O:14])[N:12]([CH2:15][CH2:16][N:17]4[CH2:22][CH2:21][N:20]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[O:29][CH3:30])[CH2:19][CH2:18]4)[CH:11]=[N:10][C:9]=3[S:31][C:6]=2[CH2:5]1)(=O)C.[OH-].[Na+]>Cl>[CH3:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[N:20]1[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][N:12]2[C:13](=[O:14])[C:8]3[C:7]4[CH2:32][CH2:33][NH:4][CH2:5][C:6]=4[S:31][C:9]=3[N:10]=[CH:11]2)[CH2:18][CH2:19]1

Participants

Conditions

Temperature: 100 °C

Procedure

4.0 g (8.6 mmol) of 3,4,5,6,7,8-hexahydro-7-acetyl-3-[2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl]pyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-one were dissolved in 80 ml of 10% strength hydrochloric acid and stirred at a bath temperature of 100° C. for 2 h. The mixture was then poured into ice-water, made alkaline with concentrated sodium hydroxide solution and extracted twice with methylene chloride. The combined organic phases were dried and concentrated. 3.7 g of crude product were isolated and were recrystallized from 50 ml of isopropanol. 2.4 g (66%) of product with melting point 168-170° C. were obtained.

Workup

extractionextracted twice with methylene chloride
customThe combined organic phases were dried
concentrationconcentrated
custom3.7 g of crude product were isolated
customwere recrystallized from 50 ml of isopropanol

Sources & evidence

ORD record: ord-97d180a953214980a616361d4140656c
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06222034B1

Reaction notes

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