Sodium Cyanide → 4-[(4-Methoxyphenyl)(methyl)amino]quinazoline-2-carbonitrile

HRID 1876152ノート

反応式

HRID 1876152 の反応式
Cl.Cl[C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[C-]#N.[Na+].[N:26]12CCN(CC1)C[CH2:27]2>CS(C)=O.CC(O)C.O.C(OCC)(=O)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:13]([CH3:14])[C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=[C:3]([C:27]#[N:26])[N:12]=2)=[CH:16][CH:17]=1

参加物

8

反応物 3

HCID 8929Sodium CyanideHCID 9237DabcoHCID 86639964(2-Chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride

生成物 1

HCID 575165474-[(4-Methoxyphenyl)(methyl)amino]quinazoline-2-carbonitrile収率 139.4%

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
35 °C

実験手順

To a solution of (2-chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride (56 mg, 0.17 mmol) in 1 mL of DMSO and 0.5 mL of 2-propanol were added sodium cyanide (16 mg, 0.34 mmol) and 1,4-diazabicyclo[2.2.2]octane (9 mg, 0.084 mmol). The mixture was heated at 35° C. for 1 d with stirring. The solution was diluted with 5 mL of water and 10 mL of ethyl acetate. The organic layer was washed with water, then dried and concentrated. The resulting crude material was purified by silica gel column chromatography to give the title compound (34 mg, 70%). 1H NMR (CDCl3, 400 MHz) δ 7.85 (d, 1H, J=8.4 Hz), 7.64 (t, 1H, J=6.8 Hz), 7.14 (m, 3H), 6.96 (m, 3H), 3.86 (s, 3H), 3.61 (s, 3H); ESI-MS m/z 291 (M+H)+.

後処理

  1. washThe organic layer was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe resulting crude material was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-bfb59ba6a15e49e489559cf83a4456ce
出典データセット
uspto-grants-2012_11
特許番号
US08309562B2

反応ノート

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