Pyridine → HCID 46841203, compound

HRID 2201002Notes

Reaction equation

HRID 2201002 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:21]3[C:13](=[N:14][C:15]4[N:16]=[CH:17][N:18]=[CH:19][C:20]=43)[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:21]3[C:13](=[N:14][C:15]4[N:16]=[CH:17][N:18]=[CH:19][C:20]=43)[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 58032590HCID 58032590, compound

Product 1

HCID 46841203HCID 46841203, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

(rac)-Ethyl 6-(4-cyanophenyl)-8-methyl-6,9-dihydropyrimido[2,1-f]purine-7-carboxylate (30 mg, 0.08 mmol), 3-(trifluoromethyl)phenylboronic acid (31 mg, 0.17 mmol, 2 eq.), anhydrous copper(II) acetate (30 mg, 0.17 mmol, 2 eq.) and molecular sieve (100 mg, 4 Å) were initially charged. Under an atmosphere of argon, abs. dichloromethane (5 ml), pyridine (27 μl, 0.33 mmol, 4 eq.) and triethylamine (23 μl, 0.17 mmol, 2 eq.) were added. After 12 h of stirring, the mixture was filtered over 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, 13% of theory).

Workup

  1. filtrationthe mixture was filtered over 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, 13% of theory)

Sources & evidence

ORD record
ord-b4e0f66192f841e0829a1afcd54f8305
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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