Phenyl glycidyl ether → HCID 11678721, compound

HRID 2353161Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[C:13]4[S:18][C:17]([CH2:19][N:20]5[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[O:32]1[CH:34]([CH2:35][O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:33]1>CN(C=O)C.C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)[C:13]4[S:18][C:17]([CH2:19][N:20]5[CH2:21][CH2:22][N:23]([CH2:33][CH:34]([OH:32])[CH2:35][O:36][C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=6)[CH2:24][CH2:25]5)=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

Conditions

Temperature: 55 °C

Procedure

Treatment of 4-[2-(1H-indazol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester with HCl in DCM/MeOH yielded 2-(1H-indazol-4-yl)-4-morpholin-4-yl-6-piperazin-1-ylmethyl-thieno[3,2-d]pyrimidine. A mixture of 2-(1H-indazol-4-yl)-4-morpholin-4-yl-6-piperazin-1-ylmethyl-thieno[3,2-d]pyrimidine (150 mg) and 1,2-epoxy-3-phenoxypropane (40 mg) was suspended in 50% DMF/0.1M sodium phosphate buffer (2 mL) and shaken at 55° C. overnight. After stirring for 24 h the reaction mixture was then diluted with DCM, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography.

Workup

stirringAfter stirring for 24 h the reaction mixture
washwashed with brine
dry with materialdried (MgSO4)
customthe solvent removed in vacuo
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-c9772035dd3e43e9b8ba4e24e22cdbc6
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750002B2

Reaction notes

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