Dimethylformamide → 2-(4-(Trifluoromethoxy)phenyl)pyrimidine-5-carboxaldehyde

HRID 1496913Notes

Reaction equation

HRID 1496913 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)=[N:11][CH:12]=1.CN([CH:27]=[O:28])C>C1COCC1>[F:21][C:20]([F:23])([F:22])[O:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[N:9]=[CH:8][C:7]([CH:27]=[O:28])=[CH:12][N:11]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 574792805-Bromo-2-[4-(trifluoromethoxy)phenyl]pyrimidineHCID 178418339Butyllithium

Product 1

HCID 498521392-(4-(Trifluoromethoxy)phenyl)pyrimidine-5-carboxaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-BuLi (2.5 M, 1.88 mL, 4.7 mmol) was added to a solution of bromide 89 (1.252 g, 3.92 mmol) in THF (40 mL) at −95° C. The solution was stirred for 30 s and then DMF (5 mL) was added. The reaction was stirred at −90° C. for 20 min and then quenched with aqueous NH4Cl. The resulting mixture was partitioned between EtOAc and water, and then column chromatography of the organic portion on silica gel (eluting with 1:7 EtOAc/hexanes) gave 2-[4-(trifluoromethoxy)phenyl]-5-pyrimidinecarbaldehyde (90) (0.778 g, 74%) as a white solid: mp 114-115° C.; 1H NMR (CDCl3) δ 10.16 (s, 1H), 9.22 (s, 2H), 8.62 (d, J=9.0 Hz, 2H), 7.36 (d, J=9.0 Hz, 2H). APCI MS m/z 269 [M+H]+, 301 [M+H+MeOH]+.

Workup

  1. stirringThe reaction was stirred at −90° C. for 20 min
  2. customquenched with aqueous NH4Cl
  3. customThe resulting mixture was partitioned between EtOAc and water

Sources & evidence

ORD record
ord-1522e18946ca4cf9a29a419dcec5d0d4
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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