Ethanol → HCID 11246161, compound

HRID 378905Notes

Reaction equation

HRID 378905 reaction equation
[Na].[CH2:2]([OH:4])[CH3:3].Cl[C:6]1[N:7]=[C:8]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:9]2[N:14]=[C:13](Cl)[N:12]=[C:11]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:10]=2[N:22]=1.O.C1C[O:33][CH2:32][CH2:31]1>>[CH2:2]([O:4][C:6]1[N:7]=[C:8]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:9]2[N:14]=[C:13]([O:33][CH2:32][CH3:31])[N:12]=[C:11]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:10]=2[N:22]=1)[CH3:3]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 8028Tetrahydrofuran2×HCID 815562,6-Dichloro-4,8-di(piperidin-1-yl)pyrimido(5,4-d)pyrimidineHCID 5360545Sodium

Product 1

HCID 11246161HCID 11246161, compoundYield 84%

Procedure

Sodium metal (0.115 g, 5 mmol) was added to ethanol (0.23 g, 5 mmol) in dry THF (5 ml) and stirred until all had dissolved. Then, 2,6-dichloro-4,8-dipiperidinopyrimidopyrimidine (0.184 g, 0.5 mmol) dissolved in dry THF (10 ml) was added to the alkoxide and the mixture was heated under reflux for 18 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 an orange crystalline solid (0.167 g, 84%), m.p. 142-143° C. Found: C, 62.11; H, 7.81; N, 21.34. C20H30N6O2 requires C, 62.15; H, 7.82; N, 21.74%.

Workup

  1. dissolutionall had dissolved
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 18 hours
  4. additionwas added
  5. extractionthe product extracted into ethyl acetate (4×20 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customRecrystallisation from methanol/water

Sources & evidence

ORD record
ord-5d2e88bdcc4f4c878be1a26e31a6eac7
Source dataset
uspto-grants-2001_10
Patent number
US06297250B1

Reaction notes

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