Water → 5-(2-Chloropyrimidin-5-yloxy)valeric acid tert-butyl ester

HRID 661464

反応式

HRID 661464 の反応式
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16]Br)([CH3:10])([CH3:9])[CH3:8].[Cl:19][C:20]1[N:25]=[CH:24][C:23]([OH:26])=[CH:22][N:21]=1.O>CS(C)=O.C(OCC)(=O)C>[C:7]([O:11][C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][O:26][C:23]1[CH:22]=[N:21][C:20]([Cl:19])=[N:25][CH:24]=1)([CH3:10])([CH3:9])[CH3:8]

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 545791Tert-butyl 5-bromopentanoateHCID 145957002-Chloro-5-pyrimidinol

生成物 1

HCID 866365415-(2-Chloropyrimidin-5-yloxy)valeric acid tert-butyl ester収率 86.9%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

Potassium carbonate (2.54 g) was added to a solution of 5-bromovaleric acid tert-butyl ester (4.3 g) obtained in Reference Example 1 (1) above and 2-chloropyrimidin-5-ol (2 g) in dimethylsulfoxide (8.6 ml) and the mixture was stirred at 40° C. overnight. The reaction mixture was cooled to room temperature, water and ethyl acetate were added and the organic layer was separated, washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=49:1→9:1) to give 5-(2-chloropyrimidin-5-yloxy)valeric acid tert-butyl ester (3.82 g). MS (m/z): 287/289 [M+H]+.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe organic layer was separated
  3. washwashed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=49:1→9:1)

出典と根拠

ORDレコード
ord-a51fbf98a66c4b14a4b1ddc008decf82
出典データセット
uspto-grants-2011_12
特許番号
US08084611B2

関連ノート

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