Water → HCID 11442220, compound

HRID 378909Notes

Reaction equation

HRID 378909 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[H-].[Na+].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>[OH:4][CH2:3][CH2:2][CH2:1][O:5][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][CH2:1][CH2:2][CH2:3][OH:4])[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 104421,3-PropanediolHCID 24758Sodium hydrideHCID 815562,6-Dichloro-4,8-di(piperidin-1-yl)pyrimido(5,4-d)pyrimidine

Product 1

HCID 11442220HCID 11442220, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,3-Propane diol (0.73 ml, 10 mmol) was dissolved in dry THF (10 ml), added to sodium hydride (0.24 g, 10 mmol) and the mixture was stirred at room temperature for 6 hours 2,6-dichloro-4,8-dipiperidinopyrimidopyrimidine (0.184 g, 0.5 mmol) in dry THF (25 ml) was added and the mixture heated under reflux 72 hours. After cooling to room temperature, water (30 ml) was added and the product extracted into ethyl acetate (4×20 ml). The organic layers were combined, dried (MgSO4), filtered and solvent removed in vacuo. Purification was carried out by column chromatography on silica gel, with dichloromethane: methanol (95:5) as eluent. Subsequent recrystallisation from methanol/water gave the title compound as a cream solid (0.115 g, 51%), m.p. 154-156° C. Found: C, 59.23; H, 7.72; N, 18.79. C22H34N6O4 requires C, 59.17; H, 7.67; N, 18.82%.

Workup

  1. additionwas added
  2. temperaturethe mixture heated
  3. temperatureunder reflux 72 hours
  4. extractionthe product extracted into ethyl acetate (4×20 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customsolvent removed in vacuo
  8. customPurification
  9. customSubsequent recrystallisation from methanol/water

Sources & evidence

ORD record
ord-5e9ba6d717e0423e875c794c24f99ed9
Source dataset
uspto-grants-2001_10
Patent number
US06297250B1

Reaction notes

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