Potassium Carbonate → 6-Methyl-4-(pyrimidin-5-yloxy)picolinonitrile

HRID 1525838

反応式

HRID 1525838 の反応式
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]#[N:10])[CH:3]=1.[OH:11][C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:8][C:6]1[N:5]=[C:4]([C:9]#[N:10])[CH:3]=[C:2]([O:11][C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)[CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 565855Pyrimidin-5-olHCID 185052494-Chloro-6-methylpyridine-2-carbonitrile

生成物 1

HCID 682949096-Methyl-4-(pyrimidin-5-yloxy)picolinonitrile収率 78.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

4-chloro-6-methylpicolinonitrile (4.0 g, 26 mmol, 1.0 eq), 5-hydroxypyrimidine (5.56 g, 57.9 mmol, 2.20 eq), K2CO3 (7.24 mg, 52.4 mmol, 2.0 eq) and DMF (66 mL) were added to a reaction vessel and heated at 80° C. for 16 hours. The reaction was filtered and concentrated on silica gel (25 g). The silica gel was loaded on top of a fresh bed of silica gel and washed with 50% ethyl acetate/hexane. The solvents were removed in vacuo and the crude solid was purified by flash chromatography on silica gel to afford 4.31 g (77%) of the title compound as a pale-yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.17 (s, 1H), 8.85 (s, 2H), 7.74 (d, J=2.4 Hz, 1H), 7.32 (d, J=2.3 Hz, 1H), 2.48 (s, 3H); ES-MS [M+1]+: 213.2.

後処理

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated on silica gel (25 g)
  3. washwashed with 50% ethyl acetate/hexane
  4. customThe solvents were removed in vacuo
  5. customthe crude solid was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-d1a409b25d464bb1885dbc5bd536199f
出典データセット
uspto-grants-2015_07
特許番号
US09085562B2

関連ノート

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