Sodium Chloride → HCID 18763640, compound

HRID 431259Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])(O)=O.[Na+].[CH:41]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=1)=[CH2:42].[Na+].[Cl-]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][C:6]1[CH:5]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=[C:2](/[CH:42]=[CH:41]/[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=2)[N:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a stirred solution of 100 mg (0.5 mmol) of 2-chloro-4-methyl-6-pyrrolidin-1-yl-pyrimidine in 0.5 ml DMF under an argon atmosphere were added at RT 67 mg (0.25 mmol) tris-(o-tolyl)phosphine, 5.5 mg (0.025 mmol) palladium(II) acetate, 17 mg (0.2 mmol) NaHCO3 followed by 263 mg (2.5 mmol) 2-vinylpyridine. The mixture was heated at 130° C. for 48 h, cooled to RT and 1.5 ml saturated aqueous NaCl solution was added. The mixture was extracted 4-times with 2 ml EtOAc/Et2O (2/1), the combined organic layers were washed with saturated aqueous NaCl, dried over MgSO4 and concentrated in vacuo. The residue was applied to a silica gel column with hexane/EtOAc as eluent (gradient: 1/1 to 1/9). Combination of the purified fractions and concentration in vacuo gave 26 mg (20%) of the desired (E)-4-methyl-2-(2-pyridin-2-yl-vinyl)-6-pyrrolidin-1-yl-pyrimidine as yellow solid. ISP mass spectrum, m/e: 267.3 (M+1 calculated for C16H18N4: 267).

Workup

temperaturecooled to RT
extractionThe mixture was extracted 4-times with 2 ml EtOAc/Et2O (2/1)
washthe combined organic layers were washed with saturated aqueous NaCl
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
concentrationCombination of the purified fractions and concentration in vacuo

Sources & evidence

ORD record: ord-e796cf31b78c4179b395c0b7ab56ee81
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06657060B2

Reaction notes

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