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

HRID 1752398Notes

Reaction equation

HRID 1752398 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:18]=[C:17]([C:19]([O:21]C(C)(C)C)=[O:20])[CH:16]=[C:15]([NH:26][C@@H:27]([CH3:32])[C:28]([O:30][CH3:31])=[O:29])[N:14]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[C:15]([NH:26][C@@H:27]([CH3:32])[C:28]([O:30][CH3:31])=[O:29])[N:14]=3)=[CH:11][CH:12]=2)=[CH:33][CH:34]=1.[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[C:15]([NH:26][C@@H:27]([CH3:32])[C:28]([O:30][CH3:31])=[O:29])[N:14]=3)=[CH:11][CH:12]=2)=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71283226(S)-tert-butyl 2-(4-(4-fluorophenoxy)phenyl)-6-((1-methoxy-1-oxopropan-2-yl)amino)pyrimidine-4-carboxylate

Product 2

HCID 71283605(S)-2-(4-(4-fluorophenoxy)phenyl)-6-((1-methoxy-1-oxopropan-2-yl)amino) pyrimidine-4-carboxylic acid trifluoroacetic acid saltYield 185.9%HCID 71283606(S)-2-(4-(4-fluorophenoxy)phenyl)-6-((1-methoxy-1-oxopropan-2-yl)amino)pyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the (S)-tert-butyl 2-(4-(4-fluorophenoxy)phenyl)-6-((1-methoxy-1-oxopropan-2-yl)amino)pyrimidine-4-carboxylate (0.312 g, 0.667 mmol) in DCM (10 mL) was added TFA (5 mL, 67 mmol). After stirring for 3 days the reaction was evaporated in vacuo and the residue triturated with hexanes, filtered and dried under a stream of nitrogen to give (S)-2-(4-(4-fluorophenoxy)phenyl)-6-((1-methoxy-1-oxopropan-2-yl)amino)pyrimidine-4-carboxylic acid as the trifluoroacetic acid salt as a cream-colored powder (0.326 g, 0.620 mmol, 93%). 1H NMR (400 MHz, DMSO-d6): 8.36-8.26 (3H, m), 7.32-7.24 (2H, m), 7.20-7.13 (2H, m), 7.10-7.03 (3H, m), 4.60-4.52 (1H, m), 3.64 (3H, s), 1.45 (3H, d, J=7.2 Hz). LC/MS: m/z=412.1 [M+H]+.

Workup

  1. customwas evaporated in vacuo
  2. customthe residue triturated with hexanes
  3. filtrationfiltered
  4. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-b76709ac1b114f46b6f86601a5ccbbd6
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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