2,5-Diamino-4,6-dichloropyrimidine → HCID 178496608, compound

HRID 600444Notes

Reaction equation

HRID 600444 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH2:9])=[C:4]([Cl:10])[N:3]=1.[CH3:11][O:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([NH2:19])[CH2:15][CH2:14]1.C(=O)(O)[O-].[Na+]>C(O)CCC>[Cl:10][C:4]1[N:3]=[C:2]([NH2:1])[N:7]=[C:6]([NH:19][C@H:16]2[CH2:17][CH2:18][C@H:13]([O:12][CH3:11])[CH2:14][CH2:15]2)[C:5]=1[NH2:9]

Participants

5

Reactant 3

HCID 3010392,5-Diamino-4,6-dichloropyrimidineHCID 516892Sodium BicarbonateHCID 178496609HCID 178496609, compound

Product 1

HCID 178496608HCID 178496608, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2,5-diamino-4,6-dichloropyrimidine (6 g, 33.5 mmol), trans-4-methoxy cyclohexyl amine (4.32 g, 33.5 mmol, 1 equiv.), sodium bicarbonate (9.85 g, 117.2 mmol, 3.5 equiv.) and 1-butanol (350 mL) were heated together at 150° C. in a sealed tube. After 3 days, when the reaction appeared to be complete (by HPLC), the reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was purified by flash chromatography (silica gel, gradual elution with 96/4 methylene chloride/methanol to 90/10 methylene chloride/methanol) to give the desired product as a brown solid (69% yield). MS (EI) m/z 272 (MH)+.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by flash chromatography (silica gel, gradual elution with 96/4 methylene chloride/methanol to 90/10 methylene chloride/methanol)

Sources & evidence

ORD record
ord-7e27267da80c485eb475144a3183b98d
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

Loading…