Water → 4-(3,4-Dimethoxy-phenyl)-6-propyl-pyrimidine-2-carbonitrile

HRID 733195Notes

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+].[CH3:19][O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28].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>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:2]2[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[N:5]=[C:4]([C:11]#[N:12])[N:3]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

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 3,4-dimethoxyphenyl 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-(3,4-dimethoxy-phenyl)-6-propyl-pyrimidine-2-carbonitrile (28 mg).

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-a7a6d24a6f7a4383918c5f65b0afa36e
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589095B2

Reaction notes

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