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Dichloromethane → (rac)-7-(4-Cyanophenyl)-2-(methoxymethyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile

HRID 1046891
ノート
印刷プレビュー

反応式

HRID 1046891 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[C:16]([CH2:18][O:19][CH3:20])[N:17]=[C:13]3[NH:12][C:11]([CH3:21])=[C:10]2[C:22]#[N:23])=[CH:5][CH:4]=1)#[N:2].ClCCl.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.N1C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[C:16]([CH2:18][O:19][CH3:20])[N:17]=[C:13]3[N:12]([C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([C:28]([F:39])([F:38])[F:27])[CH:34]=3)[C:11]([CH3:21])=[C:10]2[C:22]#[N:23])=[CH:5][CH:4]=1)#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27343883-(Trifluoromethyl)phenylboronic acid2 回HCID 136355650(rac)-7-(4-Cyanophenyl)-2-(methoxymethyl)-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile

生成物 1

HCID 66628235(rac)-7-(4-Cyanophenyl)-2-(methoxymethyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒2 回HCID 1049Pyridine溶媒2 回

実験手順

Under an atmosphere of argon protective gas, (rac)-7-(4-cyanophenyl)-2-(methoxymethyl)-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile (35 mg, 114 μmol) was stirred in abs. dichloromethane (30 ml) with molecular sieve (0.5 g, 4 Å) for 1 h. 3-(Trifluoromethyl)phenylboronic acid (65 mg, 343 μmol, 3 eq.), anhydrous copper(II) acetate (62.3 mg, 343 μmol, 3 eq.), abs. pyridine (25 μl) and triethylamine (35 mg, 343 μmol, 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 (22 mg, 114 μmol, 1 eq.), anhydrous copper(II) acetate (21 mg, 114 μmol, 1 eq.) and abs. pyridine (829 μl) were then added, and the mixture was stirred at RT for a further 3 d. The reaction mixture was then filtered through kieselguhr, the filter residue was washed with dichloromethane and pyridine 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 solid (4.4 mg, 9% of theory).

後処理

  1. stirringthe mixture was stirred at RT for a further 3 d
  2. filtrationThe reaction mixture was then filtered through kieselguhr
  3. washthe filter residue was washed with dichloromethane and pyridine
  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 solid (4.4 mg, 9% of theory)

出典と根拠

ORDレコード
ord-b447bd4db3064615a340c88a6cded0ac
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08569314B2

反応ノート

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