Water → 2-(4-((2-Amino-4-((2,4,6-triisopropylbenzenesulfonyl)oxy)-6-methylpyrimidin-5-yl)methyl)phenyl)acetonitrile

HRID 445053Notes

Reaction equation

HRID 445053 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.[CH:20]([C:23]1[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[C:25]([CH:32]([CH3:34])[CH3:33])[C:24]=1[S:35](Cl)(=[O:37])=[O:36])([CH3:22])[CH3:21].C1N2CCN(CC2)C1.O>C1COCC1.C(#N)C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][S:35]([C:24]2[C:25]([CH:32]([CH3:33])[CH3:34])=[CH:26][C:27]([CH:29]([CH3:31])[CH3:30])=[CH:28][C:23]=2[CH:20]([CH3:22])[CH3:21])(=[O:37])=[O:36])[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

Participants

7

Reactant 4

HCID 962Water3×HCID 9237DabcoHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 178433372HCID 178433372, compound

Product 1

HCID 866479282-(4-((2-Amino-4-((2,4,6-triisopropylbenzenesulfonyl)oxy)-6-methylpyrimidin-5-yl)methyl)phenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

A suspension of the product from step (ii) (6.0 g, 23.6 mmol), 2,4,6-triisopropylbenzenesulfonyl chloride (9.28 g, 30.6 mmol) and DABCO (4.76 g, 42.5 mmol) in THF (48.0 g) was stirred at 30° C. for 7 hours. Water (9.6 g) was added to the mixture and the organic layer was separated and concentrated under reduced pressure to give a solid. The solid was dissolved in acetonitrile (57.0 g) and heated to 60° C. Water (36.0 g) was added to the solution and the mixture was stirred at 60° C. for 1 hour. Water (36.0 g) was added to the mixture and the mixture was cooled to 5° C. and stirred at 5° C. for 1 hour. The resulting precipitate was collected by filtration, washed duplicate with combined solution of water (9.0 g) and acetonitrile (3.6 g), and dried to give the subtitle is compound as a solid, 11.6 g.

Workup

  1. customthe organic layer was separated
  2. concentrationconcentrated under reduced pressure
  3. customto give a solid
  4. temperatureheated to 60° C
  5. stirringthe mixture was stirred at 60° C. for 1 hour
  6. temperaturethe mixture was cooled to 5° C.
  7. stirringstirred at 5° C. for 1 hour
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed duplicate with combined solution of water (9.0 g) and acetonitrile (3.6 g)
  10. customdried
  11. customto give the subtitle

Sources & evidence

ORD record
ord-1acdc72d829b415bb07dea0f4f98e01d
Source dataset
uspto-grants-2013_07
Patent number
US08476288B2

Reaction notes

Loading…