Water → HCID 11441249, compound

HRID 378908Notes

Reaction equation

HRID 378908 reaction equation
[Na].[CH2:2]([OH:5])[CH:3]=[CH2:4].Cl[C:7]1[N:8]=[C:9]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[C:10]2[N:15]=[C:14](Cl)[N:13]=[C:12]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:11]=2[N:23]=1.O.[CH2:31]1C[O:34][CH2:33][CH2:32]1>>[CH2:2]([O:5][C:7]1[N:8]=[C:9]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[C:10]2[N:15]=[C:14]([O:34][CH2:33][CH:32]=[CH2:31])[N:13]=[C:12]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:11]=2[N:23]=1)[CH:3]=[CH2:4]

Participants

6

Reactant 5

HCID 962WaterHCID 7858Allyl AlcoholHCID 8028Tetrahydrofuran2×HCID 815562,6-Dichloro-4,8-di(piperidin-1-yl)pyrimido(5,4-d)pyrimidineHCID 5360545Sodium

Product 1

HCID 11441249HCID 11441249, compoundYield 40%

Procedure

Sodium metal (0.115 g, 5 mmol) was added to allyl alcohol (0.291 g, 5 mmol) in dry THF (5 ml) and stirred until all had dissolved. 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 heated under reflux for 72 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 white crystalline solid (0.079 g, 40%), m.p. 109-110° C.

Workup

  1. dissolutionall had dissolved
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 72 hours
  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-670965ebf7de4aa69d0cc16d81fd3387
Source dataset
uspto-grants-2001_10
Patent number
US06297250B1

Reaction notes

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