Tert-Butylamine → HCID 178449969, compound

HRID 1484984Notes

Reaction equation

HRID 1484984 reaction equation
[CH:1]1([C:4]2[CH:9]=[C:8]([OH:10])[N:7]=[C:6]([C:11]3[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=3)[N:5]=2)[CH2:3][CH2:2]1.[C:20]([NH2:24])([CH3:23])([CH3:22])[CH3:21]>C(Cl)Cl.O>[C:20]([NH:24][S:16]([C:14]1[S:15][C:11]([C:6]2[N:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[CH:9]=[C:8]([OH:10])[N:7]=2)=[CH:12][CH:13]=1)(=[O:18])=[O:17])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 178527427HCID 178527427, compound

Product 1

HCID 178449969HCID 178449969, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of crude 5-(4-cyclopropyl-6-hydroxypyrimidin-2-yl)thiophene-2-sulfonyl chloride (1.9 g, 6.0 mmol, 1.0 equiv.), t-butylamine (25 mL) and TEA (10 mL) in CH2Cl2 (500 mL) was stirred at rt for 2 h. The reaction mixture was diluted with water, the organic layer was washed (brine), dried (Na2SO4), evaporated and purified by silica gel chromatography (EA/PE 1:1) to afford N-tert-butyl-5-(4-cyclopropyl-6-hydroxypyrimidin-2-yl)thiophene-2-sulfonamide (500 mg, 24%). LC-MS (m/z)=354.1 [M+H]+

Workup

  1. washthe organic layer was washed (brine)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. custompurified by silica gel chromatography (EA/PE 1:1)

Sources & evidence

ORD record
ord-cfce642bcd6c48c2818d137ab55cd157
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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