Sodium hydride → 2-Oxo-1-trityl-1,2-dihydropyrimidin-4-yl 2,4,6-triisopropylbenzenesulfonate

HRID 2059846Notes

Reaction equation

HRID 2059846 reaction equation
[H-].[Na+].[C:3]([N:22]1[CH:27]=[CH:26][C:25](=[O:28])[NH:24][C:23]1=[O:29])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:30]([C:33]1[CH:38]=[C:37]([CH:39]([CH3:41])[CH3:40])[CH:36]=[C:35]([CH:42]([CH3:44])[CH3:43])[C:34]=1[S:45](Cl)(=[O:47])=[O:46])([CH3:32])[CH3:31].[Cl-].[NH4+]>C1COCC1.CCOC(C)=O>[CH:30]([C:33]1[CH:38]=[C:37]([CH:39]([CH3:40])[CH3:41])[CH:36]=[C:35]([CH:42]([CH3:44])[CH3:43])[C:34]=1[S:45]([O:28][C:25]1[CH:26]=[CH:27][N:22]([C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:23](=[O:29])[N:24]=1)(=[O:47])=[O:46])([CH3:31])[CH3:32]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 585799241-tritylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 585798862-Oxo-1-trityl-1,2-dihydropyrimidin-4-yl 2,4,6-triisopropylbenzenesulfonateYield 52.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (0.494 g, 12.3 mmol) was added to a stirred solution of 1-tritylpyrimidine-2,4(1H,3H)-dione (1.75 g, 4.9 mmol) in dry THF (75 mL) at RT. After stirring the mixture at RT for 45 min, 2,4,6-triisopropylbenzene-1-sulfonyl chloride (2.99 g, 9.9 mmol) was added and stirring continued at RT for 2 h. The reaction mixture was poured into a stirred mixture of EtOAc and saturated ammonium chloride solution. The organic layer was dried (MgSO4), concentrated and the residue was subjected to flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient) to afford 2-oxo-1-trityl-1,2-dihydropyrimidin-4-yl 2,4,6-triisopropylbenzenesulfonate 4A (1.6 g, 52% yield) as a white solid.

Workup

  1. stirringstirring
  2. waitcontinued at RT for 2 h
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6a181169f3f64d25a46067be15bf994e
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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