Water → {2-[4-(4-Chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidin-4-yl}-(3-morpholin-4-ylmethyl-phenyl)-amine

HRID 70084

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[CH:13]=2)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:28][CH:27]=1.C(N(C(C)C)CC)(C)C.O>O1CCOCC1>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([N:32]2[CH2:37][CH2:36][N:35]([C:2]3[N:3]=[C:4]([NH:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]5[CH2:24][CH2:23][O:22][CH2:21][CH2:20]5)[CH:13]=4)[C:5]4[S:10][CH2:9][CH2:8][C:6]=4[N:7]=3)[CH2:34][CH2:33]2)=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 160 °C

Procedure

1.09 g (2-chloro-6,7-dihydro-thieno[3,2-d]pyrimidin-4-yl)-(3-morpholin-4-ylmethyl-phenyl)-amine, 1.77 g 1-(4-chloro-phenyl)-piperazine and 1.03 ml diisopropylethylamine are placed in 12 ml dioxane, then heated in the microwave for 1 hour at 160° C. Then water is added and the mixture is extracted with dichloromethane. The organic phase is separated off using a phase transfer cartridge and evaporated to dryness. The residue is crystallised with methanol. 1.17 g of the product are obtained as a powder (m.p 177°-178° C.).

Workup

extractionthe mixture is extracted with dichloromethane
customThe organic phase is separated off
customevaporated to dryness
customThe residue is crystallised with methanol

Sources & evidence

ORD record: ord-93c7529518f747ddae0315de49d1c673
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822474B2

Linked notes

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