Potassium Carbonate → HCID 67120138, compound

HRID 2042218Notes

Reaction equation

HRID 2042218 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[CH:16][C:17]4[S:22][CH:21]=[C:20]([C:23]5[CH:34]=[CH:33][C:26]([CH2:27]CS([O-])(=O)=O)=[CH:25][CH:24]=5)[C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:41]([N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)[CH3:42]>CN(C)C=O.C(OCC)(=O)C>[CH2:41]([N:43]1[CH2:48][CH2:47][N:46]([CH2:27][C:26]2[CH:25]=[CH:24][C:23]([C:20]3[C:18]4[N:19]=[C:14]([NH:13][C:10]5[CH:11]=[N:12][C:7]([N:4]6[CH2:5][CH2:6][O:1][CH2:2][CH2:3]6)=[CH:8][CH:9]=5)[N:15]=[CH:16][C:17]=4[S:22][CH:21]=3)=[CH:34][CH:33]=2)[CH2:45][CH2:44]1)[CH3:42]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 86673217HCID 86673217, compound

Product 1

HCID 67120138HCID 67120138, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

4-(2-(6-Morpholinopyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)benzylmethanesulfonate (30 mg, 0.06 mmol) was dissolved in N,N-dimethylformamide (1 mL) and potassium carbonate (17 mg, 0.12 mmol) and 1-ethylpiperazine (38 μL, 0.30 mmol) were added. The reaction mixture was stirred at 80° C. for a day, diluted with ethyl acetate, and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (5% methanol/dichloromethane) yielded the target compound (22 mg, 70% yield).

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered with celite
  4. concentrationconcentrated
  5. customPurification by chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-30bad26db6bc43cda06d1172b5784455
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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