Potassium Carbonate → HCID 118863110, compound

HRID 63931Notes

Reaction equation

HRID 63931 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][OH:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][CH2:24][OH:25])[C:10]=3[O:9][C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)=[CH:4][CH:3]=1.BrCCCO[CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1.[C:46]([O-:49])([O-])=O.[K+].[K+]>CN(C=O)C.CC(=O)OCC.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][O:20][CH:4]4[CH2:3][CH2:2][CH2:34][CH2:46][O:49]4)[C:12](=[O:21])[N:11]([CH2:22][CH2:23][CH2:24][O:25][CH:42]4[CH2:43][CH2:44][CH2:45][CH2:40][O:41]4)[C:10]=3[O:9][C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)=[CH:33][CH:34]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 118863117HCID 118863117, compound2×

Product 1

HCID 118863110HCID 118863110, compoundYield 128.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1,3-bis(3-hydroxypropyl)furo[2,3-d]-pyrimidine-2,4(1H,3H)-dione (Compound 27, Step 7, 77.4 mg, 0.2 mmol) in DMF (4 mL) was added 2-(3-bromo propoxy)tetrahydro-2H-pyran (88.8 mg, 0.4 mmol) and K2CO3 (55.2 mg, 0.24 mmol). The reaction was stirred at RT for 2 h then diluted with EA (10 mL) and water (3 mL). The organic layer was washed with brine (3 mL), dried over Na2SO4 and concentrated to give 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1,3-bis(3-(tetrahydro-2H-pyran-2-yloxy)propyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (86.4 mg, 64% yield) as a yellow solid. LCMS: MH+ 671 and TR=2.435 min. Used without further purification.

Workup

  1. washThe organic layer was washed with brine (3 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-09a69d37187347518a2d0e9d68bce370
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

Loading…