Methyl N-(triethylammoniosulfonyl)carbamate → HCID 57722610, compound

HRID 1986861Notes

Reaction equation

HRID 1986861 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][C:12]3[N:13]([N:15]=[CH:16][C:17]=3[C:18]([NH2:20])=O)[CH:14]=2)=[CH:5][CH:4]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[N:11][C:12]3[N:13]([N:15]=[CH:16][C:17]=3[C:18]#[N:20])[CH:14]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamate2×HCID 57722607HCID 57722607, compound

Product 1

HCID 57722610HCID 57722610, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-(4-methoxy-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid amide (1-3, 150 mg, 0.56 mmol, 1 equiv) in dioxane (50 mL) was heated to reflux. After the solid was solvated, Burgess reagent (134 mg, 0.56 mmol, 1.0 equiv) was added. More Burgess reagent (4 equivalents) was added in three equal portions over 3 hours after which TLC indicated the starting amide had been consumed. The solvent was removed in vacuo and the yellow residue was partitioned between EtOAc (2×200 mL) and water (330 mL). The combined organic layers were dried over sodium sulfate and concentrated. The yellow residue was then suspended in ether and filtered to afford 6-(4-methoxy-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carbonitrile (1-4).

Workup

  1. customhad been consumed
  2. customThe solvent was removed in vacuo
  3. customthe yellow residue was partitioned between EtOAc (2×200 mL) and water (330 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-a9d0b63d11954caea41b5833b88d69a0
Source dataset
uspto-grants-2009_06
Patent number
US07550470B2

Reaction notes

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