2-Mesitylenesulfonyl chloride → 2-Amino-6-methyl-5-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)benzyl)pyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

HRID 1617187Notes

Reaction equation

HRID 1617187 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]([CH2:29][O:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)=[CH:25][CH:24]=2)=[C:17]([CH3:37])[N:16]=1>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:21][C:19]1[C:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][O:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)=[CH:25][CH:24]=2)=[C:17]([CH3:37])[N:16]=[C:15]([NH2:14])[N:20]=1)(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 130462-Mesitylenesulfonyl chlorideHCID 178433373HCID 178433373, compound

Product 1

HCID 866768952-Amino-6-methyl-5-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)benzyl)pyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Mesitylenesulfonyl chloride (3.65 g) was added to a stirred mixture of the product from step (ii) (5 g), TEA (4.2 ml) and DMAP (0.2 g) in DCM (100 ml) at rt under nitrogen. The mixture was stirred at rt for 4 h then partitioned between DCM and water. The organics were separated, washed with aq NaHCO3 soln, water, dried and evaporated under reduced pressure to afford the subtitle compound, 6.49 g.

Workup

  1. customthen partitioned between DCM and water
  2. customThe organics were separated
  3. washwashed with aq NaHCO3 soln
  4. dry with materialwater, dried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-52fe6ab8d752458abd459d7055c16459
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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