Ethanol → HCID 178478190, compound

HRID 2043355Notes

Reaction equation

HRID 2043355 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH:10]([C:12]1[N:13]=[CH:14][NH:15][CH:16]=1)=O.C(O)C.[BH4-].[Na+]>ClCCl.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([NH:1][CH2:10][C:12]2[N:13]=[CH:14][NH:15][CH:16]=2)[N:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 655222-Amino-4,6-dichloropyrimidineHCID 764281H-Imidazole-4-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 178478190HCID 178478190, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-amino-4,6-dichloropyrimidine (1.00 g, 7.72 mmol) in dichloromethane (8 ml) were added 4-formylimidazole (0.74 g, 7.72 mmol) and tetraisopropyl orthotitanate (2.86 ml, 9.65 mmol). After stirring the mixture at 40° C. overnight ethanol (8 ml) and sodium borohydride (0.38 g, 10.0 mmol) were added. The reaction mixture was stirred 40° C. for 7 hours. Then mixture was concentrated in vacuo and the residue was purified by flash chromatography (methanol/dichloromethane gradient) to yield white crystals (43 mg, 26%); MS (EI): 247.1 (37Cl M+.), 245.1 (37Cl35Cl M+.), 243.1 (35Cl M+.).

Workup

  1. additionwere added
  2. concentrationThen mixture was concentrated in vacuo
  3. customthe residue was purified by flash chromatography (methanol/dichloromethane gradient)

Sources & evidence

ORD record
ord-b1651686212e42da858c6c83d723b07d
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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