Pivaloyl chloride → 2-pivaloyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
Reaction equation
N[C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[CH3:12][C:13]([CH3:18])([CH3:17])[C:14](Cl)=[O:15]>N1C=CC=CC=1>[C:14]([C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1)(=[O:15])[C:13]([CH3:18])([CH3:17])[CH3:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 100 ml round bottom flask was charged 4.0 g (23.8 mmol) of 2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidine dissolved in 50 ml of anhydrous pyridine. To this solution was added 10.2 ml (83 mmol) of trimethylacetyl chloride, and after several minutes a precipitate began forming. The reaction was stirred at RT under a nitrogen atmosphere for 30 min. The volatiles were removed in vacuo, and the residue was dissolved in 1 L of CHCl3, washed twice with 0.1 N HCl, dried over Na2SO4, and removed in vacuo. The crude residue was flash chromatographed on silica gel eluting with a gradient of 100% CHCl3 to 2% MeOH/CHCl3. After collecting the correct fractions, the solvents were removed in vacuo to give 4.4 g (73%) of 2-pivaloyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidine as an off-white solid.
Workup
- customafter several minutes a precipitate began forming
- customThe volatiles were removed in vacuo
- dissolutionthe residue was dissolved in 1 L of CHCl3
- washwashed twice with 0.1 N HCl
- dry with materialdried over Na2SO4
- customremoved in vacuo
- customchromatographed on silica gel eluting with a gradient of 100% CHCl3 to 2% MeOH/CHCl3
- customAfter collecting the correct fractions
- customthe solvents were removed in vacuo
Sources & evidence
- ORD record
- ord-d5082ce289154f6b8326e8ee1087fe32
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05196424
Reaction notes
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