Water → HCID 11213568, compound

HRID 378906Notes

Reaction equation

HRID 378906 reaction equation
[Na].[CH3:2][CH:3]([CH3:7])[CH2:4][CH2:5][OH:6].Cl[C:9]1[N:10]=[C:11]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:12]2[N:17]=[C:16](Cl)[N:15]=[C:14]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:13]=2[N:25]=1.[OH2:32]>C1COCC1>[CH3:2][CH:3]([CH3:7])[CH2:4][CH2:5][O:6][C:9]1[N:10]=[C:11]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:12]2[N:17]=[C:16]([O:32][CH2:5][CH2:4][CH:3]([CH3:7])[CH3:2])[N:15]=[C:14]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:13]=2[N:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31260Isoamyl AlcoholHCID 815562,6-Dichloro-4,8-di(piperidin-1-yl)pyrimido(5,4-d)pyrimidineHCID 5360545Sodium

Product 1

HCID 11213568HCID 11213568, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium metal (0.115 g, 5 mmol) was added to 3-methylbutan-1-ol (0.44 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 yellow crystalline solid (0.148 g, 63%), m.p. 105-106° C. Found: C, 66.73; H, 8.80; N, 17.48. C26H42N6O2 requires C, 66.35; H, 8.99; N, 17.86%.

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-1dc5d39a38f64a96acd838053467d755
Source dataset
uspto-grants-2001_10
Patent number
US06297250B1

Reaction notes

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