Pivaloyl chloride → HCID 178447243, compound

HRID 1510920Notes

Reaction equation

HRID 1510920 reaction equation
[NH2:1][C:2]1[NH:7][C:6]2=[N:8][CH:9]=[CH:10][C:5]2=[C:4]([Cl:11])[N:3]=1.[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>N1C=CC=CC=1>[Cl:11][C:4]1[N:3]=[C:2]([NH:1][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[NH:7][C:6]2=[N:8][CH:9]=[CH:10][C:5]=12

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 178508434HCID 178508434, compound

Product 1

HCID 178447243HCID 178447243, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine (7.3 g, 43.61 mmol) in anhydrous pyridine (120 mL) was added pivaloyl chloride (18.7 mL, 152.63 mmol). The reaction was stirred at RT under nitrogen for 16 h and quenched with MeOH (50 mL). The solvents were then removed in vacuo, and the residue was co-evaporated with toluene (100 mL). The resulting residue was dissolved in EtOAc (150 mL) and washed with 0.1 M HCl (3×75 mL). The organic layer was dried (MgSO4) and evaporated. The crude material was resolved by silica chromatography (30% EtOAc/hexane) to yield 9a (12.2 g) as a white crystalline solid.

Workup

  1. customquenched with MeOH (50 mL)
  2. customThe solvents were then removed in vacuo
  3. dissolutionThe resulting residue was dissolved in EtOAc (150 mL)
  4. washwashed with 0.1 M HCl (3×75 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-58eb44f798ba4bdca0709d104ae3db8a
Source dataset
uspto-grants-2012_07
Patent number
US08212020B2

Reaction notes

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