2,4-Dichloropyrimidine → HCID 59674122, compound

HRID 1391549Notes

Reaction equation

HRID 1391549 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[N:4]=[C:3]1[NH2:12].C([O-])(O)=O.[Na+].[Cl:18][C:19]1[N:24]=[C:23](Cl)[CH:22]=[CH:21][N:20]=1>C1COCC1.C(O)C>[Cl:18][C:19]1[N:24]=[C:23]([NH:11][C:9]2[CH:8]=[CH:7][C:6]3[N:2]([CH3:1])[C:3]([NH2:12])=[N:4][C:5]=3[CH:10]=2)[CH:22]=[CH:21][N:20]=1

Participants

6

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 45078395HCID 45078395, compound

Product 1

HCID 59674122HCID 59674122, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-Methyl-1H-benzoimidazole-2,5-diamine (0.63 g, 3.89 mmol) in THF (4 ml) and ethanol (12 ml) was added NaHCO3 (0.98 g, 11.67 mmol) and 2,4-dichloropyrimidine (1.45 g, 9.7 mmol) and the reaction was heated to 80° 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)-1-methyl-1H-benzoimidazole-2,5-diamine as an red solid. MS (ESI) m/z=275 [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-ba0dc941420e473fa7a0b2b10f4dd9a6
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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