Potassium Carbonate → HCID 86710211, compound

HRID 2168216Notes

Reaction equation

HRID 2168216 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[C:10]([C:11]#[N:12])[C:3]=12.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C>[Cl:1][C:2]1[C:3]2[C:10]([C:11]#[N:12])=[CH:9][N:8]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178510331HCID 178510331, compound

Product 1

HCID 86710211HCID 86710211, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-chloro-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile D42 (60 mg) and potassium carbonate (282 mg, 2.04 mmol) were dissolved in DMF (6 ml), {2-[(chloromethyl)oxy]ethyl}(trimethyl)silane (69 mg, 0.41 mmol) was added dropwise. The reaction mixture was stirred at R.T. for 16 hours. The reaction mixture was poured onto water (30 ml), extracted with EtOAc (60 ml). Organic layer was washed with water (3×20 ml), brine (20 ml), dried (Na2SO4), filtered and concentrated in vacuo to obtain a yellow oil of desired product D43 in 105 mg. LCMS [MH+] [email protected] min (5 min run)

Workup

  1. additionThe reaction mixture was poured onto water (30 ml)
  2. extractionextracted with EtOAc (60 ml)
  3. washOrganic layer was washed with water (3×20 ml), brine (20 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f659b162e1414dc0a5cf2c54bd3bfdf0
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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