Pyridine → HCID 46841205, compound

HRID 2201012Notes

Reaction equation

HRID 2201012 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[CH:15]=[CH:16][N:17]=[C:13]3[NH:12][C:11]([CH3:18])=[C:10]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:5][CH:4]=1)#[N:2].[F:24][C:25]([F:36])([F:35])[C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.N1C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[N:14]3[CH:15]=[CH:16][N:17]=[C:13]3[N:12]([C:30]3[CH:29]=[CH:28][CH:27]=[C:26]([C:25]([F:36])([F:35])[F:24])[CH:31]=3)[C:11]([CH3:18])=[C:10]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471Triethylamine2×HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 58032564HCID 58032564, compound

Product 1

HCID 46841205HCID 46841205, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

(rac)-Ethyl 5-(4-cyanophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-6-carboxylate (152 mg, 0.49 mmol), 3-(trifluoromethyl)phenylboronic acid (187 mg, 0.1 mmol, 2 eq.), anhydrous copper(II) acetate (181 mg, 0.1 mmol, 2 eq.) and molecular sieve (200 mg, 4 Å) were initially charged. Under an atmosphere of argon protective gas, abs. dichloromethane (5 ml), pyridine (80 μl, 0.1 mmol, 2 eq.) and triethylamine (137 μl, 0.1 mmol, 2 eq.) were added. After 12 h of stirring, more anhydrous copper(II) acetate (181 mg, 0.1 mmol, 2 eq.) and triethylamine (137 μl, 0.1 mmol, 2 eq.) were added, and the mixture was stirred for a further 48 h. The reaction was then filtered through kieselguhr, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.05% TFA). After lyophilization, the product was obtained as a solid (26 mg, 12% of theory).

Workup

  1. stirringthe mixture was stirred for a further 48 h
  2. filtrationThe reaction was then filtered through kieselguhr
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.05% TFA)
  5. customAfter lyophilization, the product was obtained as a solid (26 mg, 12% of theory)

Sources & evidence

ORD record
ord-87d2506aeaff472ebde7754f16518743
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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