2-Mesitylenesulfonyl chloride → 2-Amino-5-(4-(cyanomethyl)benzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

HRID 1617206Notes

Reaction equation

HRID 1617206 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[CH:12][CH:11]=2)=[C:4]([CH3:19])[N:3]=1.[C:20]1([CH3:32])[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[S:28](Cl)(=[O:30])=[O:29]>CN(C1C=CN=CC=1)C>[CH3:32][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[S:28]([O:8][C:6]1[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[CH:12][CH:11]=2)=[C:4]([CH3:19])[N:3]=[C:2]([NH2:1])[N:7]=1)(=[O:29])=[O:30]

Participants

4

Reactant 2

HCID 130462-Mesitylenesulfonyl chlorideHCID 178433372HCID 178433372, compound

Product 1

HCID 866334092-Amino-5-(4-(cyanomethyl)benzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of the product from step (iii) (3.4 g), 2-mesitylenesulfonyl chloride (3.51 g), TEA (5.59 ml) and DMAP (82 mg) was stirred at rt for 18 h. The mixture was partitioned between DCM/water, the organics separated, washed with aq. NaHCO3 soln, water, dried and evaporated under reduced pressure. The residue was triturated with ether/ethylacetate and filtered to afford the subtitle compound, 5.08 g.

Workup

  1. customThe mixture was partitioned between DCM/water
  2. washthe organics separated, washed with aq. NaHCO3 soln
  3. dry with materialwater, dried
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with ether/ethylacetate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-56e7f408f75a429e975bf492f100f989
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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