Water → HCID 11245295, compound

HRID 378904Notes

Reaction equation

HRID 378904 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:5]2[N:10]=[C:9](Cl)[N:8]=[C:7]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[C:6]=2[N:18]=1.[CH3:25][O-:26].[Na+].O.C1[CH2:33][O:32]CC1>>[CH3:25][O:26][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:5]2[N:10]=[C:9]([O:32][CH3:33])[N:8]=[C:7]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[C:6]=2[N:18]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 815562,6-Dichloro-4,8-di(piperidin-1-yl)pyrimido(5,4-d)pyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 11245295HCID 11245295, compoundYield 46%

Procedure

2,6-Di chloro-4,8-dipiperidinopyrimidopyrimidine (0.184 g, 0.5 mmol) was dissolved in dry THF (15 ml), then added to freshly prepared sodium methoxide (4.1 ml, 1.22M, 5 mmol) in dry THF (5 ml) under a N2 atmosphere, and the mixture heated under reflux for 20 hours. After cooling to room temperature water (20 ml) was added and the product extracted into ethyl acetate (4×20 ml). The organic layers were combined, dried (MgSO4), filtered and the solvent removed in vacuo. Recrystallisation from methanol/water yielded the title compound as a yellow crystalline solid (0.083 g, 46%), m.p. 130-131° C. Found: C, 59.41; H, 7.27; N, 22.17. C18H26N6O2 requires C, 60.32; H, 7.31; N, 23.44%.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 20 hours
  3. additionwas added
  4. extractionthe product extracted into ethyl acetate (4×20 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customRecrystallisation from methanol/water

Sources & evidence

ORD record
ord-9aeec610a0924d688260c6419c6626cc
Source dataset
uspto-grants-2001_10
Patent number
US06297250B1

Reaction notes

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