1,1'-Carbonyldiimidazole → HCID 57612649, compound

HRID 2074183Notes

Reaction equation

[N:1]1([C:10]2[N:15]=[C:14]([NH:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:13]([NH2:23])=[C:12]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C1N=CN([C:35](N2C=NC=C2)=[O:36])C=1>C1COCC1>[N:1]1([C:10]2[N:15]=[C:14]3[C:13]([NH:23][C:35](=[O:36])[N:16]3[CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[C:12]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

To 30 mg (0.078 mmol) of crude 2-(1H-benzo[d]imidazol-1-yl)-6-phenyl-N4-(tetrahydro-2H-pyran-4-yl)pyrimidine-4,5-diamine in 3 mL THF was added CDI (38 mg, 0.233 mmol, 3 equiv.) and the reaction mixture was stirred at 50° C. for 18 h. The solvent was removed in vacuo and the residue purified by preparative TLC (silica gel, 5% methanol in methylene chloride) to afford the desired product (9.5 mg, 30% yield). 1H NMR (300 MHz, CDCl3) δ, ppm: 9.16 (br s, 1H), 8.68 (d, 1H), 8.06 (br m, 2H), 7.90 (d, 1H), 7.71-7.62 (m, 3H), 7.52-7.33 (m, 3H), 4.82-4.68 (m, 1H), 4.31-4.20 (m, 2H), 3.64 (app t, 2H), 3.01-2.82 (m, 2H), 1.89 (br d, 2H); MS (EI) m/z 413.2 (MH)+.

Workup

customThe solvent was removed in vacuo
customthe residue purified by preparative TLC (silica gel, 5% methanol in methylene chloride)

Sources & evidence

ORD record: ord-2ede60f2ff6e41c8b50537df52939f15
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919490B2

Reaction notes

Loading…