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Sodium Bicarbonate → (4-Benzyloxy-3,5-dimethyl-phenyl)-(6-chloro-pyrimidin-4-yl)-methanone

HRID 469302
ノート
印刷プレビュー

反応式

HRID 469302 の反応式
C([Li])CCC.[CH2:6]([O:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17](Br)=[CH:16][C:15]=1[CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CON(C)[C:26]([C:28]1[CH:33]=[C:32]([Cl:34])[N:31]=[CH:30][N:29]=1)=[O:27].C(=O)([O-])O.[Na+]>C1COCC1>[CH2:6]([O:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([C:26]([C:28]2[CH:33]=[C:32]([Cl:34])[N:31]=[CH:30][N:29]=2)=[O:27])=[CH:16][C:15]=1[CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 229631332-(Benzyloxy)-5-bromo-1,3-dimethylbenzeneHCID 581812166-Chloro-pyrimidine-4-carboxylic acidmethoxy-methyl-amideHCID 178418339Butyllithium

生成物 1

HCID 58181140(4-Benzyloxy-3,5-dimethyl-phenyl)-(6-chloro-pyrimidin-4-yl)-methanone

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
-75 °C

実験手順

Under an argon atmosphere 2.8 mL (4.5 mmol) of a 1.6 M n-butyllithium solution were added to a mixture of 1.2 g (4.0 mmol) 2-benzyloxy-5-bromo-1,3-dimethyl-benzene in mL THF cooled to −75° C. and the mixture was stirred for 1 h at −75° C. Then 0.96 g (4.3 mmol) 6-chloro-pyrimidine-4-carboxylic acidmethoxy-methyl-amide, dissolved in 10 mL THF, were added dropwise. After another 30 min stirring at −75° C. the reaction mixture was slowly heated to 0° C. The mixture was combined with saturated sodium hydrogen carbonate solution and extracted with diethyl ether. The organic phase was dried and evaporated down. The residue was purified by flash chromatography.

後処理

  1. additionwere added dropwise
  2. stirringAfter another 30 min stirring at −75° C. the reaction mixture
  3. temperaturewas slowly heated to 0° C
  4. extractionextracted with diethyl ether
  5. customThe organic phase was dried
  6. customevaporated down
  7. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-511a463b0c884810943719051e0c5e50
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08629137B2

反応ノート

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