Pivaloyl chloride → HCID 178447243, compound

HRID 2289839Notes

Reaction equation

HRID 2289839 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>[C:12]([NH: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)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 178508434HCID 178508434, compound

Product 1

HCID 178447243HCID 178447243, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine (20 g, 118 mmol) and pivaloyl chloride (14.3 g, 118 mmol) in pyridine (150 mL) was stirred for 18 hours at ambient temperature. The resulting dark red solution was evaporated to an amber solid which was co-evaporated with water (20 mL, 3×). The resulting solid was filtered, washed with cold water and then dried over KOH in vacuo to yield 22 g (83%) of 2-pivaloylamino-4-chloro-pyrrolo[2,3-d]pyrimidine as a reddish solid. 1H-NMR (DMSO-d6): δ 12.35 (bs, 1, N (7)-H); 10.07 (s,1, N (2)-H); 7.56 (m,1, H-6); 6.58 (m,1, H-5); 1.24 (s, 9, pivaloyl methyls). mp>210° C.

Workup

  1. customThe resulting dark red solution was evaporated to an amber solid which
  2. filtrationThe resulting solid was filtered
  3. washwashed with cold water
  4. dry with materialdried over KOH in vacuo

Sources & evidence

ORD record
ord-e0f8d61a8926405c9d4cd60ba4e781a0
Source dataset
uspto-grants-2000_07
Patent number
US06093807

Reaction notes

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