Tetrahydrofuran → HCID 16119573, compound

HRID 491487Notes

Reaction equation

HRID 491487 reaction equation
[CH:1]([C:4]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([C:21]#[C:22][Si](C)(C)C)=[CH:15][C:5]=1[O:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1)([CH3:3])[CH3:2].[F-].[Cs+].C1COCC1>O>[C:21]([C:16]1[C:17]([O:19][CH3:20])=[CH:18][C:4]([CH:1]([CH3:2])[CH3:3])=[C:5]([CH:15]=1)[O:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1)#[CH:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 25953Cesium fluorideHCID 57678393HCID 57678393, compound

Product 1

HCID 16119573HCID 16119573, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(2-Isopropyl-4-methoxy-5-trimethylsilanylethynyl-phenoxy)-pyrimidine-2,4-diamine (0.75 g, 2 mmol) and Cesium Fluoride (0.46 g, 3 mmol) were added to 10 mL of dry THF under nitrogen, and the reaction mixture was stirred for 6 hours at room temperature. The reaction mixture was poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed on 50 g of flash silica (3%-6% MeOH/CH2Cl2) to give 0.54 g of 5-(5-ethynyl-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine, MS (M+H)=299.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on 50 g of flash silica (3%-6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-05c7cc3a2f974eac8c444acfe2d4b4bb
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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