Bis-(1H-imidazol-2-YL)-methanone → 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

HRID 600434Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:4][C:5]([N:15]2[C:19]3[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=3[N:17]=[CH:16]2)=[N:6][C:7]=1[NH:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[C:30](C1NC=CN=1)(C1NC=CN=1)=[O:31]>C1COCC1>[F:24][C:21]1[CH:22]=[CH:23][C:18]2[N:17]=[CH:16][N:15]([C:5]3[N:6]=[C:7]4[C:2]([NH:1][C:30](=[O:31])[N:8]4[CH:9]4[CH2:10][CH2:11][O:12][CH2:13][CH2:14]4)=[C:3]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:4]=3)[C:19]=2[CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 5-amino-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-6-(tetrahydro-2H-pyran-4-ylamino)pyrimidine-4-carboxylate (800 mg, 2.0 mmol) in dry THF (10 mL) was added carbonyl diimidazole (2.0 g) and the mixture was stirred at 60° C. for 48 h in a sealed tube. The solvent was evaporated and water (25 mL) was added to the residue. Filtration and drying of the white solid gave 600 mg (51% yield) of desired product. 1H NMR (400 MHz, DMSO-d6) δ, ppm: 11.89 (s, 1H), 9.09 (s, 1H), 8.84 (dd, J=2.8, 2.4 Hz, 1H), 7.78 (dd, J=5.2, 5.2 Hz, 1H), 7.23 (m, 1H), 4.63 (m, 1H), 4.49 (q, J=6.8 Hz, 2H), 4.40 (dd, J=4.0, 3.0 Hz, 2H), 3.51 (t, J=11.6 Hz, 2H), 2.52 (m, 2H), 1.80 (d, J=2 Hz, 2H), 1.41 (t, J=7.1 Hz, 3H); LCMS (EI) m/z 427 (MH)+.

Workup

customThe solvent was evaporated
additionwater (25 mL) was added to the residue
filtrationFiltration
customdrying of the white solid

Sources & evidence

ORD record: ord-adf8e0046f0845d6a5dc07012a523065
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902187B2

Reaction notes

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