Pivaloyl chloride → HCID 178418603, compound

HRID 6524Notes

Reaction equation

HRID 6524 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][C:9]([NH2:11])=[CH:10][C:3]=12.[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>N1C=CC=CC=1>[OH:1][C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][C:9]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:10][C:3]=12

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 178418658HCID 178418658, compound

Product 1

HCID 178418603HCID 178418603, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3.0 g (0.02 mole) of 4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidine and 8.4 g (0.07 mol) of pivaloyl chloride in 40 mL of pyridine is stirred for 30 minutes at from 80° to 90° C., the mixture then evaporated to dryness, and the residue dissolved in 30 mL of methanol. Addition of 10% aqueous ammonia yields 4.2 g (89%) of 4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine which can be further purified by chromatography through silica gel, eluting with 8% methanol in methylene p chloride. mp 295° C. 1NMR (d6 -DMSO) δ1.20(s, 9H), 6.37(d, J=3.4Hz, 1H), 6.92(d, J=3.4Hz, 1H), 10.78 (s, 1H), 11.56 (s, 1H), 11.82 (s, 1H). Anal. Calc. for C11H14N4O2C, 56.40; H, 6.02; N, 23.92. Found: C, 56.16; H, 6.01; N, 23.67.

Workup

  1. customthe mixture then evaporated to dryness
  2. dissolutionthe residue dissolved in 30 mL of methanol
  3. additionAddition of 10% aqueous ammonia

Sources & evidence

ORD record
ord-35982a95451c4e8385f818981ea12a16
Source dataset
uspto-grants-1993_09
Patent number
US05248775

Reaction notes

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