5-bromo-2-chloro-3-methylpyrimidin-4(3H)-one → 5-bromo-2-(cyclohexylmethyl)-3-methylpyrimidin-4(3H)-one

HRID 2241306ノート

反応式

HRID 2241306 の反応式
[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5](Cl)=[N:6][CH:7]=1.[Br-].[CH:12]1([CH2:18][Zn+])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5]([CH2:18][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:6][CH:7]=1

参加物

5

反応物 2

HCID 673486115-bromo-2-chloro-3-methylpyrimidin-4(3H)-oneHCID 178419774HCID 178419774、化合物

生成物 1

HCID 685170185-bromo-2-(cyclohexylmethyl)-3-methylpyrimidin-4(3H)-one収率 37%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

A solution of 5-bromo-2-chloro-3-methylpyrimidin-4(3H)-one (0.100 g, 0.448 mmol; prepared according to the procedure of Example 46, Step B) and PdCl2(PPh3)2 (0.016 g, 0.022 mmol) in THF (2.5 mL) was sparged with N2, and then (cyclohexylmethyl)zinc(II)bromide (0.904 ml, 0.452 mmol; 0.5 M solution in THF) was added. The reaction mixture was stirred at 100° C. for 1.5 hours. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and H2O. The aqueous layer was re-extracted with EtOAc (1×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude material was purified by flash column chromatography, eluting with 10:1 CH2Cl2/EtOAc to afford 0.047 g (37%) of the product as a waxy yellow solid. LRMS (APCI pos) m/e 285, 287 (M+, Br pattern).

後処理

  1. customprepared
  2. customwas sparged with N2
  3. temperatureThe reaction mixture was cooled to room temperature
  4. custompartitioned between EtOAc and H2O
  5. extractionThe aqueous layer was re-extracted with EtOAc (1×)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by flash column chromatography
  10. washeluting with 10:1 CH2Cl2/EtOAc

出典と根拠

ORDレコード
ord-5d5d19c72f8d4f228e95fe0e925768ef
出典データセット
uspto-grants-2010_05
特許番号
US07723330B2

反応ノート

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