2,4-Dichloropyrimidine → HCID 86601116, compound

HRID 1391527Notes

Reaction equation

HRID 1391527 reaction equation
[CH:1]([NH:4][C:5]1[N:9]([CH3:10])[C:8]2[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][C:7]=2[N:6]=1)([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[Cl:21][C:22]1[N:27]=[C:26](Cl)[CH:25]=[CH:24][N:23]=1>C1COCC1.C(O)C>[Cl:21][C:22]1[N:27]=[C:26]([NH:15][C:13]2[CH:12]=[CH:11][C:8]3[N:9]([CH3:10])[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:6][C:7]=3[CH:14]=2)[CH:25]=[CH:24][N:23]=1

Participants

6

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 59674126N2-isopropyl-1-methyl-1H-benzimidazole-2,5-diamine

Product 1

HCID 86601116HCID 86601116, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of N2-isopropyl-1-methyl-1H-benzimidazole-2,5-diamine (1.46 g, 7.2 mmol) in THF (7 ml) and ethanol (21 ml) was added NaHCO3 (1.81 g, 21.6 mmol) and 2,4-dichloropyrimidine (2.68 g, 18 mmol) and the reaction was heated to 75° C. After 5 h, the reaction was filtered hot and concentrated to a gray foam. Ether was added and the solid was filtered and dried to give N5-(2-chloro-pyrimidin-4-yl)-N2-isopropyl-1-methyl-1H-benzimidazole-2,5-diamine as an off-white solid. N5-(2-chloro-pyrimidin-4-yl)-N2-isopropyl-1-methyl-1H-benzimidazole-2,5-diamine was dissolved in DMF (21 ml) and cesium carbonate (6.84 g, 21 mmol) was added After 15 min, iodomethane (0.70 ml, 11.2 mmol) was added, and the reaction was stirred at rt. After TLC showed the starting material to be consumed, the reaction was diluted with water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, dried over MgSO4 and concentrated to a red foam. The crude material was purified with silica gel to give the title compound as a white solid (1.10 g, 46% over two steps). 1H NMR (300 MHz, d6-DMSO) δ 7.87 (d, J=6.0 Hz, 1H), 7.22 (d, J=8.1 Hz, 1H), 7.11 (1.8 Hz, 1H), 6.82 (dd, J=8.1 and 1.8 Hz, 1H), 6.53 (d, J=7.5 Hz, 1H), 6.09 (d, J=6.0 Hz, 1H), 4.04 (m, 1H), 3.51 (s, 3H), 3.37 (s, 3H), 1.23 (d, J=6.6 Hz, 6H). MS (ESI) m/z=331 [M+H]+.

Workup

  1. filtrationthe reaction was filtered hot
  2. concentrationconcentrated to a gray foam
  3. additionEther was added
  4. filtrationthe solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-5398d686bb14405e83e628fb3b16d397
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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