Reaction #487541

Reaction equation

DIAD

methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-hydroxybenzoate

tert-butyl 6-hydroxyhexylcarbamate

Triphenylphosphine

→

methyl 2-(6-(tert-butoxycarbonylamino)hexyloxy)-4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate

Yield 36.0%

Solvents

DCM

Conditions

Workup

1. 1
   OtherThe solvent was removed under vacuum
2. 2
   Otherthe crude product was purified by silica gel chromatography
3. 3
   OtherThe product fractions were collected
4. 4
   Otherthe solvent was removed under vacuum

Procedure

methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-hydroxybenzoate (100 mg, 0.264 mmol), tert-butyl 6-hydroxyhexylcarbamate (68.9 mg, 0.317 mmol), Triphenylphosphine (139 mg, 0.528 mmol), were dissolved in DCM then DIAD (0.103 mL, 0.528 mmol) was added. The reaction was stirred for 16 h. The solvent was removed under vacuum and the crude product was purified by silica gel chromatography using 20% EtOAc/Hexanes. The product fractions were collected and the solvent was removed under vacuum to give 55 mg (36%) methyl 2-(6-(tert-butoxycarbonylamino)hexyloxy)-4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate.

Source