Pyridine → HCID 46841073, compound

HRID 2201003Notes

Reaction equation

HRID 2201003 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[C:15]4[N:16]=[CH:17][N:18]=[CH:19][C:20]=4[N:21]=[C:13]3[NH:12][C:11]([CH3:22])=[C:10]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5][CH:4]=1)#[N:2].[F:28][C:29]([F:40])([F:39])[C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=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[C:15]4[N:16]=[CH:17][N:18]=[CH:19][C:20]=4[N:21]=[C:13]3[N:12]([C:34]3[CH:33]=[CH:32][CH:31]=[C:30]([C:29]([F:40])([F:39])[F:28])[CH:35]=3)[C:11]([CH3:22])=[C:10]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 58032621HCID 58032621, compound

Product 1

HCID 46841073HCID 46841073, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

(rac)-Ethyl 9-(4-cyanophenyl)-7-methyl-6,9-dihydropyrimido[1,2-e]purine-8-carboxylate (20 mg, 55 μmol), 3-(trifluoromethyl)phenylboronic acid (21 mg, 0.11 mmol, 2 eq.), anhydrous copper(II) acetate (20 mg, 0.11 mmol, 2 eq.) and molecular sieve (50 mg, 4 Å) were initially charged. Under an atmosphere of argon, abs. dichloromethane (2 ml), pyridine (18 μl, 0.22 mmol, 4 eq.) and triethylamine (15 μl, 0.11 mmol, 2 eq.) were added. After 12 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-0.1% TFA). After lyophilization, the product was obtained as a solid (5.6 mg, 19% 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-0.1% TFA)
  4. customAfter lyophilization, the product was obtained as a solid (5.6 mg, 19% of theory)

Sources & evidence

ORD record
ord-db3c71d6a5994c168ba15019ce4c69df
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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