Ethyl 2-(6-fluoro-1h-benzo[d]imidazol-1-yl)-5-nitro-6-(tetrahydro-2h-pyran-4-ylamino)pyrimidine-4-carboxylate → ethyl 5-amino-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-6-(tetrahydro-2H-pyran-4-ylamino)pyrimidine-4-carboxylate

HRID 600433Notes

Reaction equation

HRID 600433 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13]([N+:21]([O-])=O)=[C:12]([NH:24][CH:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[N:11]=3)[C:6]=2[CH:31]=1.[H][H]>C(O)C.[Pd]>[NH2:21][C:13]1[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:15][C:10]([N:7]2[C:6]3[CH:31]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[N:9]=[CH:8]2)=[N:11][C:12]=1[NH:24][CH:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1

Participants

5

Reactant 2

HCID 57612691Ethyl 2-(6-fluoro-1h-benzo[d]imidazol-1-yl)-5-nitro-6-(tetrahydro-2h-pyran-4-ylamino)pyrimidine-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57612710ethyl 5-amino-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-6-(tetrahydro-2H-pyran-4-ylamino)pyrimidine-4-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogenation of ethyl 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-5-nitro-6-(tetrahydro-2H-pyran-4-ylamino)pyrimidine-4-carboxylate (310 mg, 0.717 mmol) was performed in ethanol, using Pd/C (10%), under a positive pressure of hydrogen. After 10 h, the catalyst was filtered, washed with portions of methylene chloride, and the combined filtrate concentrated to give the desired amine as a white solid (220 mg, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ, ppm: 8.97 (s, 1H), 8.47 (dd, J=2.6, 2.2 Hz, 1H), 7.74 (m, 1H), 7.60 (d, J=8.9 Hz, 2H), 7.16 (m, 1H), 6.74 (d, J=8.3 Hz, 1H), 4.37-4.32 (m, 3H), 3.94 (d, J=10.4 Hz, 2H), 3.55 (t, J=10.4 Hz, 2H), 2.01 (m, 2H), 1.58 (m, 2H), 1.42 (t, J=7.1 Hz, 3H); LCMS (EI) m/z 401 (MH)+.

Workup

  1. filtrationthe catalyst was filtered
  2. washwashed with portions of methylene chloride
  3. concentrationthe combined filtrate concentrated

Sources & evidence

ORD record
ord-12542cb61f9a470c91f54aa450fb3df4
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

Loading…