2-methoxy-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine → 2-Methoxy-7H-pyrrolo[2,3-d]pyrimidine

HRID 273347Notes

Reaction equation

HRID 273347 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[CH2:11][CH2:10][NH:9][C:7]=2[N:8]=1>C(Cl)Cl.CCOCC.O=[Mn]=O>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[CH:11]=[CH:10][NH:9][C:7]=2[N:8]=1

Participants

5

Reactant 1

HCID 691945832-methoxy-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 101033172-Methoxy-7H-pyrrolo[2,3-d]pyrimidineYield 90%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

MnO2 (1.720 g, 20 mmol) was added to 2-methoxy-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine in 20 mL of anhydrous CH2Cl2 at room temperature. The mixture was stirred for 8 h, diluted with anhydrous ether (50 mL), and filtered through a pad of Celite. The filtrate was concentrated in vacuo, and the residue was purified on a silica gel column eluting with MeOH/CH2Cl2 (1:9) to give 2-methoxy-7H-pyrrolo[2,3-d]pyrimidine (0.149 g, 90%).

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified on a silica gel column
  4. washeluting with MeOH/CH2Cl2 (1:9)

Sources & evidence

ORD record
ord-d5cc0d00db344232bd1195d256711000
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

Loading…