2,4-Dichloropyrimidine → Tert-butyl 5-[(2-chloropyrimidin-4-yl)amino]-1-methyl-1H-benzimidazol-2-yl(phenyl)carbamate

HRID 1391532Notes

Reaction equation

[NH2:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([CH3:23])[C:7]([N:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:8][C:4]=2[CH:3]=1.C([O-])(O)=O.[Na+].[Cl:31][C:32]1[N:37]=[C:36](Cl)[CH:35]=[CH:34][N:33]=1>C1COCC1.C(O)C>[Cl:31][C:32]1[N:37]=[C:36]([NH:1][C:2]2[CH:25]=[CH:24][C:5]3[N:6]([CH3:23])[C:7]([N:9]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[N:8][C:4]=3[CH:3]=2)[CH:35]=[CH:34][N:33]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of tert-butyl 5-amino-1-methyl-1H-benzimidazol-2-yl(phenyl)carbamate (1.03 g, 3.0 mmol) in THF (3 ml) and ethanol (9 ml) was added NaHCO3 (0.76 g, 9.0 mmol) and 2,4-dichloropyrimidine (0.89 g, 6.0 mmol) and the reaction was heated to 75° C. After 5 h, the reaction was filtered hot and concentrated to a gray foam. The crude material was purified on silica gel to give the title compound as a white foam (0.98 g, 73%). 1H NMR (300 MHz, d6-DMSO) δ 10.00 (s, 1H), 8.10 (d, J=5.7 Hz, 1H), 7.89 (s, 1H), 7.58 (d, J=9.0 Hz, 1H), 7.36-7.39 (m, 5H), 7.24-7.34 (m, 1H), 6.70 (d, J=6.0 Hz, 1H), 3.73 (s, 3H), 1.40 (s, 9H).

Workup

filtrationthe reaction was filtered hot
concentrationconcentrated to a gray foam
customThe crude material was purified on silica gel

Sources & evidence

ORD record: ord-d23938f8f7c94165a015e425725d2150
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338959B2

Reaction notes

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