Water → 4-(2-Chloro-5-(trifluoromethyl)phenyl)-6-propylpyrimidine-2-carbonitrile

HRID 733196Notes

Reaction equation

I[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[N:5]=[C:4]([C:11]#[N:12])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1B(O)O.O>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][C:25]=1[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[N:5]=[C:4]([C:11]#[N:12])[N:3]=1

Participants

Conditions

Temperature: 105 °C

Procedure

Under nitrogen atmosphere, a solution (c=0.18 M) of 4-iodo-6-propyl-pyrimidine-2-carbonitrile (1 mL, 0.18 mmol) in degassed toluene, an aqueous solution (c=2 M) of potassium carbonate (0.225 mL, 0.45 mmol) and tetrakis(triphenylphosphine) palladium (10 mg, 0.09 mmol) were successively added to a solution (c=0.216 M) of 2-chloro-5-(trifluoromethyl)phenyl boronic acid (1 ml, 0.216 mmol) in degassed toluene. The mixture was heated at 105° C. for 4 h, then was allowed to cool to room temperature and mixed with water (4 mL). The organic layer was evaporated under reduced pressure. The residue was chromatographed by preparative HPLC (H2O+0.05% TFA/CH3CN+0.05% TFA) to afford 4-(2-chloro-5-trifluoromethyl-phenyl)-6-propyl-pyrimidine-2-carbonitrile (34 mg, 58%) as a solid.

Workup

temperatureto cool to room temperature
customThe organic layer was evaporated under reduced pressure
customThe residue was chromatographed by preparative HPLC (H2O+0.05% TFA/CH3CN+0.05% TFA)

Sources & evidence

ORD record: ord-da720f3f061c4bad80b59edcf116d58d
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589095B2

Reaction notes

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