Ethanol → HCID 136344414, compound

HRID 1022457Notes

Reaction equation

HRID 1022457 reaction equation
Cl[C:2]1[NH:3][C:4](=[O:19])[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[N:7]=1.C(O)C.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>C(Cl)Cl.CO>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][N:33]([C:2]2[NH:3][C:4](=[O:19])[C:5]3[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=3[N:7]=2)[CH2:32][CH2:31]1

Participants

6

Reactant 3

HCID 702EthanolHCID 705291-(2-Fluorophenyl)piperazineHCID 136344411HCID 136344411, compound

Product 1

HCID 136344414HCID 136344414, compoundYield 40.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A high pressure reaction vial was charged with 2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (50 mg, 175 μmol) and ethanol (460 μL). The reaction was treated with 1-(2-fluorophenyl)piperazine (63.1 mg, 55.3 μL, 350 μmol) and was sealed. The reaction was then heated to 100° C. where it stirred overnight. At this time, the reaction was allowed to cool to room temperature. It was then diluted with methylene chloride and methanol and concentrated in vacuo onto Celite®. Flash chromatography (12 g silica gel column, 1-10% methylene chloride/methanol) afforded 2-(4-(2-fluorophenyl)piperazin-1-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one as a purple oil (31.5 mg, 40.6%). 1H NMR (400 MHz, DMSO-d6) δ ppm −0.32-0.07 (m, 9H) 0.84 (t, J=8.01 Hz, 2H) 3.07 (br. s., 4H) 3.51 (t, J=8.01 Hz, 2H) 3.73 (br. s., 4H) 5.34 (s, 2H) 6.31 (d, J=3.52 Hz, 1H) 6.89 (d, J=3.52 Hz, 1H) 6.95-7.25 (m, 4H) 10.83-11.10 (m, 1H). LC-MS calcd. for C22H31FN5O2S [(M+H)+] 444, obsd. 444.1.

Workup

  1. customA high pressure reaction
  2. customwas sealed
  3. temperatureto cool to room temperature
  4. concentrationconcentrated in vacuo onto Celite®

Sources & evidence

ORD record
ord-699c2bdc860049b0a63a54a5034adcd4
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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