Trifluoroacetic acid → 5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-amine

HRID 2353698Notes

Reaction equation

HRID 2353698 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[N:11]=[C:10]([C:19]2[S:23][C:22]([N:24](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)=[N:21][CH:20]=2)[N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[N:11]=[C:10]([C:19]2[S:23][C:22]([NH2:24])=[N:21][CH:20]=2)[N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59477211tert-butyl N-[5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate

Product 1

HCID 593799205-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-amineYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl N-[5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate (1.7 g, 2.9 mmol) and TFA (8 mL) in DCM (15 mL) was stirred at RT for 16 hours. The solvent was removed under reduced pressure and the residue made basic with aqueous ammonia solution. The product was extracted with ethyl acetate, the organics dried over sodium sulphate, filtered and evaporated to give the desired material as a white solid (1 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionThe product was extracted with ethyl acetate
  3. dry with materialthe organics dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0525d6864a134c8493549c71a558136a
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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