Potassium Carbonate → HCID 89579633, compound

HRID 928603Notes

Reaction equation

HRID 928603 reaction equation
[CH3:1][S:2]([C:5]1[N:6]=[C:7](S(C)(=O)=O)[C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][O:11][C:9]=2[N:10]=1)(=[O:4])=[O:3].[N:24]1([CH2:29][CH2:30][O:31][CH2:32][CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:28][CH2:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][S:2]([C:5]1[N:6]=[C:7]([N:36]2[CH2:37][CH2:38][CH:33]([CH2:32][O:31][CH2:30][CH2:29][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:34][CH2:35]2)[C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][O:11][C:9]=2[N:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 623388724-(2-Pyrrolidin-1-ylethoxymethyl)piperidineHCID 69223068HCID 69223068, compound

Product 1

HCID 89579633HCID 89579633, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

2,4-Bis(methylsulphonyl)-5-phenyl-furo[2,3-d]-pyrimidine (400 mg, 1.14 mmol) in acetonitrile (10.0 mL) was treated with 4-(2-pyrrolidine-1-ylethyloxymethyl)piperidine (360 mg, 1.7 mmol) and potassium carbonate (219 mg, 1.71 mmol) and heated in a microwave at 120° C. for 30 min. The reaction was concentrated in vacuum to a gum and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried over sodium sulphate and concentrated in vacuum to a gum. The gum was purified by preparative HPLC (basic method 6) to yield methylsulfonyl-5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]furo[2,3-d]pyrimidine (96 mg, 0.198 mmol, 17%). 1H NMR (CDCl3) δ: 1.07 (2H, m), 1.52 (2H, br d, J=8 Hz), 1.75 (5H, br s), 2.5 (4H, b s), 2.6 (2H, t, J=5 Hz), 2.8 (2H, t, J=8 Hz), 3.18 (2H, d, J=4 Hz), 3.35 (3H, s), 3.5 (2H, t, J=4 Hz), 4.05 (2H, d, J=8 Hz), 7.4 (5H, m), 7.6 (1H, s).

Workup

  1. concentrationThe reaction was concentrated in vacuum to a gum
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuum to a gum
  6. customThe gum was purified by preparative HPLC (basic method 6)

Sources & evidence

ORD record
ord-0ca55ee3e9c34675b5c8c3289c5bbbba
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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