Water → HCID 11374128, compound

HRID 378907Notes

Reaction equation

HRID 378907 reaction equation
[Na].[CH3:2][CH:3]([CH3:6])[CH2:4][OH:5].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]>C1COCC1>[CH3:2][CH:3]([CH3:6])[CH2:4][O:5][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:31][CH2:2][CH:3]([CH3:6])[CH3:4])[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 4

HCID 962WaterHCID 6560IsobutanolHCID 815562,6-Dichloro-4,8-di(piperidin-1-yl)pyrimido(5,4-d)pyrimidineHCID 5360545Sodium

Product 1

HCID 11374128HCID 11374128, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium metal (0.115 g, 5 mmol) was added to 2-methylpropan-1-ol (0.37 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 42 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 (0.122 g, 54%), m.p. 114-116° C.

Workup

  1. dissolutionall had dissolved
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 42 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-6c2d3e4d571148f58b9557b8d4025bf0
Source dataset
uspto-grants-2001_10
Patent number
US06297250B1

Reaction notes

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