Allyl iodide → 4-Chloro-7-(prop-2-en-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 2227252Notes

Reaction equation

HRID 2227252 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[CH2:13](I)[CH:14]=[CH2:15]>C1COCC1>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH2:15][CH:14]=[CH2:13])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 184732904-Chloro-7-(prop-2-en-1-yl)-7H-pyrrolo[2,3-d]pyrimidineYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.3 g: 8.5 mmol) in dry THF (30 ml) was added sodium hydride (1.0 g, 0.25 mmol, 60% dispersion in mineral oil). After stirring at ambient temperature for 1 hour, allyl iodide (0.93 ml, 10 mmol) was added and stirring continued for 48 hours. The mixture was concentrated in vacuo, triturated in hot ethyl acetate, and filtered. The filtrate was concentrated in vacuo to give an orange solid residue. The solid was triturated in CH2Cl2 and filtered to afford 4-chloro-7-allyl-pyrrolo[2,3-d]pyrimidine as a light yellow powder (0.58 g, 36%): TS-MS: 194 (MH+).

Workup

  1. stirringstirring
  2. waitcontinued for 48 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customtriturated in hot ethyl acetate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto give an orange solid residue
  8. customThe solid was triturated in CH2Cl2
  9. filtrationfiltered

Sources & evidence

ORD record
ord-a8fce8aecdaf495d8d78f9ee14335c14
Source dataset
uspto-grants-2002_07
Patent number
US06413971B1

Reaction notes

Loading…