Potassium Carbonate → HCID 23582515, compound

HRID 1435958Notes

Reaction equation

HRID 1435958 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:16][C:15]3[CH2:14][C@H:13]([CH2:17][O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[NH:12][C:11](=[O:26])[C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1.C1OCCOCCOCCOCCOCCOC1.C([O-])([O-])=O.[K+].[K+].[C:51]([CH2:55]OS(C(F)(F)F)(=O)=O)([F:54])([F:53])[F:52]>CN(C=O)C.O>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:16]([CH2:55][C:51]([F:54])([F:53])[F:52])[C:15]3[CH2:14][CH:13]([CH2:17][O:18][CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:12][C:11](=[O:26])[C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 25194016HCID 25194016, compound

Product 1

HCID 23582515HCID 23582515, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred mixture of (R)-2-(2-amino-pyrimidin-4-yl)-6-benzyloxymethyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (73 mg, 0.21 mmol) in dry DMF (2 mL) were added 18-crown-6 ether (110.5 mg, 0.42 mmol), K2CO3 (115.5 mg, 0.84 mmol) and CF3CH2OSO2CF3 (0.21 mmol). The reaction mixture was heated at 50° C. for 7 hours, then treated with water and extracted with AcOEt. The organic phase was dried over anh. Na2SO4 and evaporated to yield a crude product that was purified by flash chromatography (eluant: DCM/MeOH 95:5) to provide 64 mg of the title product.

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic phase was dried over anh. Na2SO4
  3. customevaporated
  4. customto yield a crude product that
  5. customwas purified by flash chromatography (eluant: DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-fd32f2155ee4478885b48a27eeeafb59
Source dataset
uspto-grants-2009_11
Patent number
US07618982B2

Reaction notes

Loading…