Pyridine → HCID 46841075, compound

HRID 1046896Notes

Reaction equation

HRID 1046896 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[N: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]=[N: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 1049Pyridine2×HCID 8471TriethylamineHCID 27343883-(Trifluoromethyl)phenylboronic acid2×HCID 136133147HCID 136133147, compound

Product 1

HCID 46841075HCID 46841075, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon protective gas, ethyl(rac)-7-(4-cyanophenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate (600 mg, 1.9 mmol) was stirred in abs. dichloromethane (450 ml) with molecular sieve (0.5 g, 4 Å) for 1 h. 3-(Trifluoromethyl)phenylboronic acid (1.10 g, 5.8 mmol, 3 eq.), anhydrous copper(II) acetate (1.05 g, 5.8 mmol, 3 eq.), abs. pyridine (1.25 ml, 15.5 mmol, 8 eq.) and triethylamine (0.59 g, 5.8 mmol, 3 eq.) were then added, and the mixture was stirred at RT for 12 h. More molecular sieve (0.5 g, 4 Å), 3-(trifluoromethyl)phenylboronic acid (0.37 g, 1.9 mmol, 1 eq.), anhydrous copper(II) acetate (0.35 g, 1.9 mmol, 1 eq.) and abs. pyridine (0.63 ml, 7.73 mmol, 4 eq.) were then added, and the mixture was stirred at RT for a further 12 h. The reaction mixture was then filtered through kieselguhr, the filter residue was washed with dichloromethane and methanol and the filtrate was concentrated to dryness. The residue was purified by preparative HPLC (Gromsil C18 column, 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). The product was obtained as a colorless amorphous solid (404.6 mg, 46% of theory).

Workup

  1. stirringthe mixture was stirred at RT for a further 12 h
  2. filtrationThe reaction mixture was then filtered through kieselguhr
  3. washthe filter residue was washed with dichloromethane and methanol
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe residue was purified by preparative HPLC (Gromsil C18 column, 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10)
  6. customThe product was obtained as a colorless amorphous solid (404.6 mg, 46% of theory)

Sources & evidence

ORD record
ord-4c517094b42b4e97bd6c1c86dec066cb
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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