Water → HCID 11166752, compound

HRID 378911Notes

Reaction equation

HRID 378911 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[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>[CH3:1][O:2][CH2:3][CH2:4][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][CH2:4][CH2:3][O:2][CH3:1])[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 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 815562,6-Dichloro-4,8-di(piperidin-1-yl)pyrimido(5,4-d)pyrimidine

Product 1

HCID 11166752HCID 11166752, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Methoxyethanol (0.38 g, 5 mmol) was dissolved in dry THF (5 ml) and added to sodium hydride (0.12 g, 5 mmol) and stirred for 8 hours at room temperature. 2,6-dichloro-4,8-dipiperidinopyrimidopyrimidine (0.184 g, 0.5 mmol) in dry THF (10 ml) was added to this and the mixture heated under reflux for 32 hours. After cooling to room temperature, water (30 ml) was added and the product extracted into ethyl acetate (4×20 ml), the organic layers combined, dried (MgSO4), filtered and the solvent removed in vacuo. Recrystallisation from methanol/water yielded the title compound as a white solid (0.076 g, 34%), m.p. 127-128° C. Found C, 59.31; H, 7.60; N, 18.80. C22H34N6O4 requires C, 59.17; H, 7.67; N, 18.82%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 32 hours
  3. temperatureAfter cooling to room temperature
  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-71d9e201483b4ba58813d3660bc4204a
Source dataset
uspto-grants-2001_10
Patent number
US06297250B1

Reaction notes

Loading…