Ethylene Glycol → HCID 11350617, compound

HRID 378910Notes

Reaction equation

HRID 378910 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].Cl[C:8]1[N:9]=[C:10]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:11]2[N:16]=[C:15](Cl)[N:14]=[C:13]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:12]=2[N:24]=1.[OH2:31].[CH2:32]1[CH2:36][O:35]CC1>>[OH:3][CH2:2][CH2:1][O:4][C:8]1[N:9]=[C:10]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:11]2[N:16]=[C:15]([O:35][CH2:36][CH2:32][OH:31])[N:14]=[C:13]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:12]=2[N:24]=1

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 815562,6-Dichloro-4,8-di(piperidin-1-yl)pyrimido(5,4-d)pyrimidine

Product 1

HCID 11350617HCID 11350617, compoundYield 45%

Procedure

Ethylene glycol (0.56 ml, 10 mmol) was dissolved in dry THF (10 ml), then added to sodium hydride (0.24 g, 10 mmol) and stirred at room temperature for 6 hours. 2,6-dichloro-4,8-dipiperidinopyrimidopyrimidine (0.184 g, 0.5 mmol) in dry THF (25 ml) was added and the mixture heated under reflux for 96 hours. After cooling to room temperature, water (30 ml) was added and the product extracted into ethyl acetate (4×20 ml). The organic layers were combined, dried (MgSO4), filtered and solvent removed in vacuo. Purification was carried out by column chromatography on silica gel, with dichloromethane: methanol (95:5) as eluent. This gave the title compound as an off-white solid (0.1 g, 45%), m.p. 148-150° C. Found: C, 57.54; H, 7.21; N, 19.41. C20H30N6O4 requires C, 57.40; H, 7.23; N, 20.08%.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 96 hours
  3. temperatureAfter cooling to room temperature
  4. extractionthe product extracted into ethyl acetate (4×20 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customsolvent removed in vacuo
  8. customPurification

Sources & evidence

ORD record
ord-24a85a77fe9e4ce19581a0a4d6a04154
Source dataset
uspto-grants-2001_10
Patent number
US06297250B1

Reaction notes

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