Ethyl 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purine-6-carboxylate → 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purine-6-carboxylic acid

HRID 600435Notes

Reaction equation

HRID 600435 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:18]=[C:17]4[C:13]([NH:14][C:15](=[O:25])[N:16]4[CH:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[C:12]([C:26]([O:28]CC)=[O:27])[N:11]=3)[C:6]=2[CH:31]=1>Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:18]=[C:17]4[C:13]([NH:14][C:15](=[O:25])[N:16]4[CH:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[C:12]([C:26]([OH:28])=[O:27])[N:11]=3)[C:6]=2[CH:31]=1

Participants

3

Reactant 1

HCID 57612711Ethyl 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purine-6-carboxylate

Product 1

HCID 576126552-(6-fluoro-1H-benzo[d]imidazol-1-yl)-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purine-6-carboxylate (600 mg, 1.41 mmol) in concentrated aqueous HCl (15 mL) was heated at 100° C. for 6 h. The mixture was concentrated and the residue triturated with diethyl ether. The solid formed was filtered and dried to give 7 as an off white solid. Yield: 410 mg, 73%. 1H NMR (400 MHz, DMSO-d6) δ, ppm: 11.84 (s, 1H), 9.20 (s, 1H), 8.47 (dd, J=2.4, 2.4 Hz, 1H), 7.82 (dd, J=5.2, 4.8 Hz, 1H), 7.26 (m, 1H), 4.63 (m, 1H), 4.04 (q, J=3.6 Hz, 2H), 3.51 (t, J=11.6 Hz, 2H), 2.60-2.54 (m, 2H), 1.80 (d, J=9.8 Hz, 2H); LCMS (EI) m/z 399 (MH)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue triturated with diethyl ether
  3. customThe solid formed
  4. filtrationwas filtered
  5. customdried
  6. customto give 7 as an off white solid

Sources & evidence

ORD record
ord-e0d43ab878cf41cba437021f27cf2df8
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

Loading…