Dimethylformamide → 4-((2-Amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl 2,4,6-trimethylbenzenesulfonate

HRID 1617200Notes

Reaction equation

HRID 1617200 reaction equation
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9](Cl)(=[O:11])=[O:10].[NH2:14][C:15]1[N:20]=[C:19]([OH:21])[C:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=2[O:30][CH3:31])=[C:17]([CH3:32])[N:16]=1.CN(C=O)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:13][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][C:18]2[C:19]([O:21][S:9]([C:2]3[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=3[CH3:13])(=[O:11])=[O:10])=[N:20][C:15]([NH2:14])=[N:16][C:17]=2[CH3:32])=[C:24]([O:30][CH3:31])[CH:25]=1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 130462-Mesitylenesulfonyl chloride2×HCID 178493423HCID 178493423, compound

Product 1

HCID 866334084-((2-Amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl 2,4,6-trimethylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Mesitylenesulfonyl chloride (5.25 g) was added to a mixture of the product from step (iii) (5 g), TEA (7 ml) and DMAP (120 mg) in DCM (100 ml) and stirred at rt for 24 h. DMF (10 ml) was added and the mixture heated under reflux for 12 h. Another portion of 2-mesitylenesulfonyl chloride (2 g) was added and heated under reflux for a further 24 h. The mixture was partitioned between DCM/water, the organics separated, washed with aq NaHCO3 soln, brine, dried and evaporated under reduced pressure. The residue was triturated with ether/isohexane and filtered to afford the subtitle compound, 9.515 g.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 12 h
  3. temperatureheated
  4. temperatureunder reflux for a further 24 h
  5. customThe mixture was partitioned between DCM/water
  6. washthe organics separated, washed with aq NaHCO3 soln
  7. dry with materialbrine, dried
  8. customevaporated under reduced pressure
  9. customThe residue was triturated with ether/isohexane
  10. filtrationfiltered

Sources & evidence

ORD record
ord-6deda175fdb14567b710d0152e491e44
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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