Dimethylformamide → 3-methyl-2-methylsulfanyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 33963

反応式

HRID 33963 の反応式
C(O[C:4](=[O:16])[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)C.[C:17]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)#[N:18].CC(C)([O-])C.[K+].[CH3:31][S:32]N=C=O.IC.[CH3:38][N:39]([CH3:42])C=O>>[CH3:38][N:39]1[C:4](=[O:16])[C:5]([C:6]2[CH:15]=[CH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=2)=[C:17]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[N:18]=[C:42]1[S:32][CH3:31]

参加物

7

反応物 6

HCID 6228Dimethylformamide2 回HCID 6328Methyl iodideHCID 75064-CyanopyridineHCID 256821Ethyl 2-naphthylacetateHCID 21933440MethylthioisocyanateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 223466413-methyl-2-methylsulfanyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

実験手順

To a stirring solution of ethyl-2-naphthylacetate (10.0 g, 46.7 mmol) and 4-cyanopyridine (4.86 g, 46.7 mmol) in 50 mL dry dimethylformamide (DMF) at room temperature under nitrogen was added 47 mL potassium tert-butoxide (1.0 M in 2-methyl-2-propanol) dropwise via syringe. The dark red solution was stirred at room temperature for 75 min. Methylthioisocyanate (3.41 g, 46.7 mmol) in 10 mL DMF added whole. The solution was stirred for 90 min at room temperature. Iodomethane (2.95 mL, 46.7 mmol) was added dropwise over a 3 min period. Solid precipitates out of reaction. Continued to stir as a mixture for 30 min. Water (500 mL) was slowly added to reaction mixture. The solid was collected via filtration then washed with water, cold ethanol (50 mL), and ether. The solid was air dried for 3 days. M+1=360.2.

後処理

  1. stirringThe solution was stirred for 90 min at room temperature
  2. customSolid precipitates out of reaction
  3. stirringto stir as a mixture for 30 min
  4. additionWater (500 mL) was slowly added to reaction mixture
  5. filtrationThe solid was collected via filtration
  6. washthen washed with water, cold ethanol (50 mL), and ether
  7. customdried for 3 days

出典と根拠

ORDレコード
ord-77270c2e721440a28b95e897fee0bb01
出典データセット
uspto-grants-2008_09
特許番号
US07429594B2

関連ノート

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