Potassium Iodide → Tert-butyl 2-((4-((2-amino-4-methyl-6-(2,4,6-triisopropylphenylsulfonyloxy)pyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-trifluoroethyl)amino)acetate

HRID 2207107Notes

Reaction equation

HRID 2207107 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[S:16]([O:19][C:20]1[C:25]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33]Cl)=[CH:29][C:28]=2[O:35][CH3:36])=[C:24]([CH3:37])[N:23]=[C:22]([NH2:38])[N:21]=1)(=[O:18])=[O:17])([CH3:3])[CH3:2].[F:39][C:40]([F:52])([F:51])[CH2:41][NH:42][CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(#N)C.O>[NH2:38][C:22]1[N:23]=[C:24]([CH3:37])[C:25]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][N:42]([CH2:41][C:40]([F:39])([F:51])[F:52])[CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[CH:29][C:28]=2[O:35][CH3:36])=[C:20]([O:19][S:16]([C:5]2[C:4]([CH:1]([CH3:2])[CH3:3])=[CH:9][C:8]([CH:10]([CH3:11])[CH3:12])=[CH:7][C:6]=2[CH:13]([CH3:15])[CH3:14])(=[O:18])=[O:17])[N:21]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 60680127Tert-butyl 2-[(2,2,2-trifluoroethyl)amino]acetateHCID 1179927752-Amino-5-(4-chloromethyl-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-triisopropylbenzenesulfonate

Product 1

HCID 117992617Tert-butyl 2-((4-((2-amino-4-methyl-6-(2,4,6-triisopropylphenylsulfonyloxy)pyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-trifluoroethyl)amino)acetateYield 154.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The mixture of 2-amino-5-(4-chloromethyl-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-triisopropylbenzenesulfonate (6.0 g), tert-butyl 2-(2,2,2-trifluoroethylamino)acetate (2.7 g), sodium carbonate (3.4 g) and potassium iodide (0.5 g) in acetonitrile (48 g) was refluxed for 8 h. After cooling to RT, water (30 g) was added to the mixture and extracted with toluene (48 g). The organic layer was washed with water (30 g) and concentrated in vacuo. The residue was precipitated with n-heptane (18 g) to afford the sub-title compound (12.2 g).

Workup

  1. temperaturewas refluxed for 8 h
  2. extractionextracted with toluene (48 g)
  3. washThe organic layer was washed with water (30 g)
  4. concentrationconcentrated in vacuo
  5. customThe residue was precipitated with n-heptane (18 g)

Sources & evidence

ORD record
ord-2def6d0e992348559005c3993c7fcea9
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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