Pyridine → HCID 58032584, compound

HRID 1046907Notes

Reaction equation

HRID 1046907 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N: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:8]=[CH:7][C:6]([CH:9]2[N:14]3[N: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:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 3154565HCID 3154565, compound

Product 1

HCID 58032584HCID 58032584, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

(rac)-Ethyl 7-(4-cyanophenyl)-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate (20 mg, 64 μmol), 3-(trifluoromethyl)phenylboronic acid (25 mg, 0.13 mmol, 2 eq.), anhydrous copper(II) acetate (23 mg, 0.13 mmol, 2 eq.) and molecular sieve (100 mg, 4 Å) were initially charged. Under an atmosphere of argon protective gas, abs. dichloromethane (2 ml), pyridine (10 μl, 0.13 mmol, 2 eq.) and triethylamine (18 μl, 0.13 mmol, 2 eq.) were added. After 24 h of stirring, the mixture was 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 (10.5 mg, 36% of theory).

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.05% TFA)
  4. customAfter lyophilization, the product was obtained as a solid (10.5 mg, 36% of theory)

Sources & evidence

ORD record
ord-d20523fddff94537951f39bcf416761a
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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