4-(Trifluoromethoxy)phenylboronic acid → 5-(Ethoxymethoxy)-2-[4-(trifluoromethoxy)phenyl]pyrimidine

HRID 2066634Notes

Reaction equation

HRID 2066634 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH2:11][CH3:12])=[CH:4][N:3]=1.[F:13][C:14]([F:26])([F:25])[O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1>>[CH2:11]([O:10][CH2:9][O:8][C:5]1[CH:4]=[N:3][C:2]([C:19]2[CH:18]=[CH:17][C:16]([O:15][C:14]([F:13])([F:25])[F:26])=[CH:21][CH:20]=2)=[N:7][CH:6]=1)[CH3:12]

Participants

3

Reactant 2

HCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 866505392-Chloro-5-(ethoxymethoxy)pyrimidine

Product 1

HCID 669560465-(Ethoxymethoxy)-2-[4-(trifluoromethoxy)phenyl]pyrimidineYield 91%

Procedure

Suzuki coupling of chloropyrimidine 108 (see Example 2S) and 4-(trifluoromethoxy)phenylboronic acid as in Example 2S above for 2 h, followed by chromatography of the product on silica gel, eluting with 0-2% Et2O/petroleum ether (foreruns) and then with 2% Et2O/petroleum ether, gave 5-(ethoxymethoxy)-2-[4-(trifluoromethoxy)phenyl]pyrimidine (110) (91%) as a white solid: mp (petroleum ether) 41-43° C.; 1H NMR (CDCl3) δ 8.60 (s, 2H), 8.41 (dt, J=9.0, 2.4 Hz, 2H), 7.30 (br dd, J=9.0, 0.9 Hz, 2H), 5.31 (s, 2H), 3.77 (q, J=7.1 Hz, 2H), 1.25 (t, J=7.1 Hz, 3H); HRESIMS calcd for C14H14F3N2O3 m/z [M+H]+ 315.0951. found 315.0944.

Workup

  1. customabove for 2 h
  2. washeluting with 0-2% Et2O/petroleum ether (foreruns)

Sources & evidence

ORD record
ord-cd0913bbdb0447fca7acd04f1479673c
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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