Trifluoroacetic acid → (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(4-(4-fluorophenoxy)phenyl)pyrimidine-4-carboxylic acid

HRID 1752401Notes

Reaction equation

HRID 1752401 reaction equation
[NH2:1][C:2](=[O:33])[C@@H:3]([NH:5][C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[N:9]=[C:8]([C:26]([O:28]C(C)(C)C)=[O:27])[CH:7]=1)[CH3:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2](=[O:33])[C@@H:3]([NH:5][C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[N:9]=[C:8]([C:26]([OH:28])=[O:27])[CH:7]=1)[CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71283307(S)-tert-butyl 6-((1-amino-1-oxopropan-2-yl)amino)-2-(4-(4-fluorophenoxy)phenyl)pyrimidine-4-carboxylate

Product 1

HCID 71283677(S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(4-(4-fluorophenoxy)phenyl)pyrimidine-4-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the (S)-tert-butyl 6-((1-amino-1-oxopropan-2-yl)-amino)-2-(4-(4-fluorophenoxy)phenyl)pyrimidine-4-carboxylate (0.426 g, 0.941 mmol) in DCM (10 mL) was added TFA (5 mL, 67 mmol). After stirring overnight, the reaction was evaporated in vacuo and the residue triturated with 3 mL acetonitrile, filtered, rinsed once with 1 mL acetonitrile and dried under vacuum at 40° C. to give (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(4-(4-fluorophenoxy)phenyl)pyrimidine-4-carboxylic acid as an off-white powder (0.343 g, 0.865 mmol, 92% yield). 1H NMR (400 MHz, DMSO-d6): 8.40 (2H, d, J=8.8 Hz), 8.05 (1H, d, J=6.6 Hz), 7.56 (1H, s), 7.32-7.24 (2H, m), 7.19-7.14 (2H, m), 7.11 (1H, s), 7.07-7.01 (3H, m), 4.61-4.52 (1H, m), 1.37 (3H, d, J=7.0 Hz). LC/MS: m/z=397.1 [M+H]+.

Workup

  1. customthe reaction was evaporated in vacuo
  2. customthe residue triturated with 3 mL acetonitrile
  3. filtrationfiltered
  4. washrinsed once with 1 mL acetonitrile
  5. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-307bbab4006a4be68305cc0e9ab13759
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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