Dimethyl Sulfoxide → HCID 17954678, compound

HRID 505351Notes

Reaction equation

HRID 505351 reaction equation
CS(C)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH:18][C@@H:19]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:20][N:21]1[C:26]2=[N:27][C:28]([C:32]3[CH:37]=[CH:36][N:35]=[CH:34][N:33]=3)=[CH:29][C:30](=[O:31])[N:25]2[CH2:24][CH2:23][C:22]1([CH3:39])[CH3:38].C(N(CC)CC)C>ClCCl.O>[CH3:38][C:22]1([CH3:39])[CH2:23][CH2:24][N:25]2[C:30](=[O:31])[CH:29]=[C:28]([C:32]3[CH:37]=[CH:36][N:35]=[CH:34][N:33]=3)[N:27]=[C:26]2[N:21]1[CH2:20][C:19](=[O:18])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 68697508HCID 68697508, compound

Product 1

HCID 17954678HCID 17954678, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of 0.24 ml (3.3 mmol) of dimethyl sulfoxide in 3 ml of anhydrous dichloromethane at −780° C. was added 0.42 ml (2.93 mmol) of trifluoroacetic anhydride in 2 ml of anhydrous dichloromethane and the mixture allowed to stir at −78° C. for 20 min. 0.201 g (0.53 mmol) of 9-(2(S)-Hydroxy-2-phenyl-ethyl)-8,8-dimethyl-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one in 2 ml of anhydrous dichloromethane was added at −78° C. and stirring continued for 30 min. 0.62 ml (4.47 mmol) of triethylamine was added and the mixture allowed to stir at room temperature for 12 h. Water was added and the mixture extracted with ethyl acetate, the extracts were washed with a saturated aqueous solution of ammonium chloride, a saturated aqueous solution of sodium chloride, dried and evaporated to give crude product. Purification by chromatography on silica gel eluting with ethyl acetate gave 0.045 g (23%) of pure product. Mp.: 203-205° C.

Workup

  1. stirringstirring
  2. waitcontinued for 30 min
  3. stirringto stir at room temperature for 12 h
  4. extractionthe mixture extracted with ethyl acetate
  5. washthe extracts were washed with a saturated aqueous solution of ammonium chloride
  6. dry with materiala saturated aqueous solution of sodium chloride, dried
  7. customevaporated
  8. customto give crude product
  9. customPurification by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-94b97c6bbb8b4511a7e375b2facdb180
Source dataset
uspto-grants-2010_08
Patent number
US07781440B2

Reaction notes

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