N-Methylmorpholine N-oxide monohydrate → 7-(4-[1,2-Dihydroxyethyl]-phenyl)-4-ethoxy-9-methyl-2-piperazin-1-yl-thieno[2,3-d:4,5-d']dipyrimidine

HRID 556401Notes

Reaction equation

HRID 556401 reaction equation
[CH2:1]([O:3][C:4]1[C:5]2[S:31][C:17]3[N:18]=[C:19]([C:23]4[CH:28]=[CH:27][C:26]([CH:29]=[CH2:30])=[CH:25][CH:24]=4)[N:20]=[C:21]([CH3:22])[C:16]=3[C:6]=2[N:7]=[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[N:9]=1)[CH3:2].[OH2:32].C[N+]1([O-])CC[O:37]CC1>CC(C)=O>[OH:32][CH:29]([C:26]1[CH:27]=[CH:28][C:23]([C:19]2[N:20]=[C:21]([CH3:22])[C:16]3[C:6]4[N:7]=[C:8]([N:10]5[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]5)[N:9]=[C:4]([O:3][CH2:1][CH3:2])[C:5]=4[S:31][C:17]=3[N:18]=2)=[CH:24][CH:25]=1)[CH2:30][OH:37]

Participants

4

Reactant 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 597550854-Ethoxy-9-methyl-2-piperazin-1-yl-7-(4-vinylphenyl)-thieno[2,3-d:4,5-d']dipyrimidine

Product 1

HCID 597551377-(4-[1,2-Dihydroxyethyl]-phenyl)-4-ethoxy-9-methyl-2-piperazin-1-yl-thieno[2,3-d:4,5-d']dipyrimidine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.20 g (0.46 mmol) 4-ethoxy-9-methyl-2-piperazin-1-yl-7-(4-vinylphenyl)-thieno[2,3-d:4,5-d′]dipyrimidine and 0.16 g (1.39 mmol) N-methylmorpholine-N-oxide-monohydrate were dissolved in 50 ml acetone. Then, 0.3 ml (4% aqueous) OSO4 solution was added and stirring was carried out at room temperature for 24 h. Thereafter, 100 ml 1 M NaCO3 solution were added and extraction with dichloromethane was carried out. Following flash chromatographic purification (chloroform/methanol, 8.5:1.5) 100 mg (46%) of the title compound is obtained. ESI-MS [m/z]: 466, melting point: >300° C.

Workup

  1. extractionextraction with dichloromethane
  2. customchromatographic purification (chloroform/methanol, 8.5:1.5) 100 mg (46%) of the title compound
  3. customis obtained

Sources & evidence

ORD record
ord-17a06e2d9fef4257aad6dcacba70c420
Source dataset
uspto-grants-2011_11
Patent number
US08058285B2

Reaction notes

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