Hydrochloric Acid → HCID 178517385, compound

HRID 1280584Notes

Reaction equation

HRID 1280584 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13](S(C)(=O)=O)=[N:14][CH:15]=2)[NH:10][C:9]1=[O:22].[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26][CH2:25]1.Cl>COCCOCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([NH:23][C@H:24]3[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26][CH2:25]3)=[N:14][CH:15]=2)[NH:10][C:9]1=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 184254033-(2-chloro-phenyl)-7-methylsulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneHCID 178511715HCID 178511715, compound

Product 1

HCID 178517385HCID 178517385, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
102.5 °C

Procedure

Sulfone 11.1 (0.400 g, 1.18 mmol) was combined with trans-4-aminocyclohexanol (0.272 g, 2.36 mmol) and 2-methoxyethyl ether (0.4 mL). The mixture was heated to 100-105° C. for 1 hour at which time it was cooled to room temperature and concentrated in vacuo. The residue was purified by column chromatography on silica gel using 9:1 dichloromethane/methanol. The column fractions containing product were combined and concentrated in vacuo to an oil which was re-dissolved in ethyl acetate and methanol. Addition of hydrochloric acid (1.0M/Et2O, 1.0 equivalent) gave the salt which dissolved in the solvents. The solution was concentrated in vacuo to a solid which was triturated in ether, filtered and dried to give 0.220 g of 3-(2-chlorophenyl)-7-(trans-4-hydroxycyclohexylamino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one.

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel using 9:1 dichloromethane/methanol
  4. additionThe column fractions containing product
  5. concentrationconcentrated in vacuo to an oil which
  6. dissolutionwas re-dissolved in ethyl acetate
  7. customgave the salt which
  8. dissolutiondissolved in the solvents
  9. concentrationThe solution was concentrated in vacuo to a solid which
  10. customwas triturated in ether
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-25c761c3d839423db321eecc53dfa4b3
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

Loading…