Potassium Phosphate, Tribasic → HCID 44204534, compound

HRID 1908245Notes

Reaction equation

HRID 1908245 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.Cl[C:20]1[CH:25]=[C:24](Cl)N=C[N:21]=1.FC(F)(F)O[C:30]1[CH:35]=[CH:34]C(B(O)O)=[CH:32][CH:31]=1.[O-:41]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.O.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:24]1([C@@H:25]([OH:41])[CH2:20][NH:21][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=3)[N:5]=[CH:4][N:3]=2)[CH:34]=[CH:35][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 709434,6-DichloropyrimidineHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 24902132HCID 24902132, compound

Product 1

HCID 44204534HCID 44204534, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

4-Chloro-6-(4-trifluoromethoxy-phenyl)-pyrimidine. To a suspension of 4,6-dichloropyrimidine (2.18 g, 14.7 mmol) and 4-trifluoromethoxyphenyl boronic acid (3.32 g, 16.1 mmol) in DME (72 mL) and water (18 mL) were added K3PO4 (6.24 g, 29.4 mmol) and Pd(PPh3)4 (0.51 g, 0.44 mmol). The reaction mixture was heated at 85° C. under N2 for 16 h. The reaction mixture was cooled to rt and the organic layer separated, dried (MgSO4), and concentrated. The residue was purified (FCC) to give the title compound as a yellow solid (2.20 g, 54%).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customthe organic layer separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified (FCC)

Sources & evidence

ORD record
ord-09941f28806848eaa05a569e2345f577
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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