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

HRID 2074200Notes

Reaction equation

HRID 2074200 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-737b80250c0c4d7db72e4aa7fce67bdd
Source dataset
uspto-grants-2011_04
Patent number
US07919490B2

Reaction notes

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