2,5-Diamino-4,6-dichloropyrimidine → HCID 178508448, compound

HRID 600450Notes

Reaction equation

HRID 600450 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH2:9])=[C:4](Cl)[N:3]=1.[NH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]1.C(=O)(O)[O-].[Na+]>C(O)CCC>[NH2:1][C:2]1[N:3]=[C:4]([NH:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]2)[C:5]([NH2:9])=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 3010392,5-Diamino-4,6-dichloropyrimidineHCID 516892Sodium BicarbonateHCID 178511715HCID 178511715, compound

Product 1

HCID 178508448HCID 178508448, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2,5-diamino-4,6-dichloropyrimidine (10.5 g, 58.6 mmol), trans-4-aminocyclohexanol (6.75 g, 58.6 mmol, 1 equiv.), sodium bicarbonate (17.2 g, 205 mmol, 3.5 equiv.) and 1-butanol (210 mL) were heated together at 150° C. in a sealed tube. After 3 days, when the reaction appeared to be complete (by LCMS), the reaction mixture was cooled to room temperature and the solvent was removed in vacuo. Water (150 mL) was added to the residue with stirring at room temperature for 30 min, and the dark red solid filtered under vacuo to give, after drying, 10 g (66% yield) of the desired product. 1H NMR (300 MHz, d6-DMSO) δ, ppm: 6.14 (d, 1H), 5.57 (s, 2H), 4.54 (d, 1H), 3.90 (s, 2H), 3.81-3.76 (m, 1H), 3.40-3.32 (m, 1H), 1.86-1.82 (m, 4H), 1.28-1.20 (m, 4H); MS (EI) m/z 258.1 (MH)+.

Workup

  1. customthe solvent was removed in vacuo
  2. additionWater (150 mL) was added to the residue
  3. filtrationthe dark red solid filtered under vacuo
  4. customto give
  5. customafter drying

Sources & evidence

ORD record
ord-a4aed6cad8bf4f2a92eb1a798820354e
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

Loading…