Dichloromethane → Methyl 2-(tert-butoxy)-2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

HRID 472812ノート

反応式

HRID 472812 の反応式
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:17])[C:3]=1[CH:18]([OH:23])[C:19]([O:21][CH3:22])=[O:20].C(Cl)Cl.Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[C:3]([O:23][CH:18]([C:3]1[C:4]([CH3:17])=[N:5][C:6]2[N:7]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:10]=2)[C:2]=1[Cl:1])[C:19]([O:21][CH3:22])=[O:20])([CH3:18])([CH3:4])[CH3:2]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 24247Perchloric AcidHCID 86670265Methyl 2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate

生成物 1

HCID 86670264Methyl 2-(tert-butoxy)-2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate収率 121.6%

試薬・触媒・溶媒 1

HCID 10908tert-Butyl acetate溶媒

実験手順

To a suspension of methyl 2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (100 mg, 0.301 mmol) in tert-butyl acetate (2 mL) at room temperature was added CH2Cl2 (2 mL) followed by perchloric acid (0.027 mL, 0.452 mmol). The reaction mixture was stirred for 2 h at room temperature. The reaction mixture was quenched with water and diluted with ethyl acetate. The organic phase was washed with saturated NaHCO3 and dried over sodium sulfate. The solvent was evaporated. Purification by silica gel chromatography provided the title compound (71 mg, 60.7%). 1H-NMR (500 MHz, CDCl3) δ ppm 1.27 (9H, s), 2.66 (3H, s), 3.73 (3H, s), 5.66 (1H, s), 6.93 (1H, s), 7.34-7.52 (3H, m), 8.01 (2H, d, J=7.3 Hz).

後処理

  1. customThe reaction mixture was quenched with water
  2. additiondiluted with ethyl acetate
  3. washThe organic phase was washed with saturated NaHCO3
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated
  6. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-84b3c0dbeb9e4e4291bcc78991124fb6
出典データセット
uspto-grants-2014_01
特許番号
US08633200B2

反応ノート

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