Potassium Phosphate, Tribasic → tert-Butyl-[(1R)-2-({6-[3-fluoro-4-(trifluoromethyl)phenyl]pyrimidin-4-yl}amino)-1-phenylethyl]carbamate

HRID 1400014Notes

Reaction equation

HRID 1400014 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][NH:10][C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1)([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:31]=1[C:32]([F:35])([F:34])[F:33].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][NH:10][C:11]1[CH:16]=[C:15]([C:28]2[CH:29]=[CH:30][C:31]([C:32]([F:34])([F:35])[F:33])=[C:26]([F:25])[CH:27]=2)[N:14]=[CH:13][N:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 177500503-Fluoro-4-trifluoromethyl-phenylboronic acidHCID 87214707[2-(6-Chloro-pyrimidin-4-ylamino)-1-phenyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 131732139tert-Butyl-[(1R)-2-({6-[3-fluoro-4-(trifluoromethyl)phenyl]pyrimidin-4-yl}amino)-1-phenylethyl]carbamateYield 73%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
85 °C

Procedure

[2-(6-Chloro-pyrimidin-4-ylamino)-1-phenyl-ethyl]-carbamic acid tert-butyl ester (87 mg, 0.25 mmol), 3-fluoro-4-(trifluoromethyl)-phenyl boronic acid (57 mg, 0.28 mmol), Pd(PPh3)4 (2.9 mg, 2.5 μmol) and K3PO4 (110 mg, 0.50 mmol) were placed in a sealed tube which was evacuated and refilled with N2. 1,2-Dimethoxyethane (2 mL) and water (0.5 mL) were added to the sealed tube. The reaction mixture was stirred at 85° C. overnight. The reaction mixture was cooled to rt and was filtered through a pad of MgSO4. The pad was washed with CH2Cl2. The crude filtrate was concentrated under reduced pressure and the residue was purified via reverse phase chromatography to yield the title compound (87.0 mg, 59%).

Workup

  1. customwhich was evacuated
  2. additionrefilled with N2
  3. addition1,2-Dimethoxyethane (2 mL) and water (0.5 mL) were added to the sealed tube
  4. temperatureThe reaction mixture was cooled to rt
  5. filtrationwas filtered through a pad of MgSO4
  6. washThe pad was washed with CH2Cl2
  7. concentrationThe crude filtrate was concentrated under reduced pressure
  8. customthe residue was purified via reverse phase chromatography

Sources & evidence

ORD record
ord-02a22a0f1d6845ab8774ead3535a33cc
Source dataset
uspto-grants-2014_12
Patent number
US08906914B2

Reaction notes

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