2-Amino-4,6-dichloropyrimidine → 4-Chloro-6-(2-furanyl)-2-pyrimidinamine

HRID 254151ノート

反応式

HRID 254151 の反応式
C([Sn](CCCC)(CCCC)[C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)CCC.[NH2:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[C:22]([Cl:27])[N:21]=1>CN(C=O)C.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>[NH2:19][C:20]1[N:21]=[C:22]([Cl:27])[CH:23]=[C:24]([C:6]2[O:7][CH:8]=[CH:9][CH:10]=2)[N:25]=1

参加物

5

反応物 2

HCID 655222-Amino-4,6-dichloropyrimidineHCID 43936882-(Tributylstannyl)furan

生成物 1

HCID 223243064-Chloro-6-(2-furanyl)-2-pyrimidinamine収率 57%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A solution of 2-(tributylstannyl)furan (35.7 g, 100 mmol) in DMF (100 mL) was treated with 2-amino-4,6-dichloropyrimidine (16.4 g, 100 mmol) and dichlorobis(triphenylphosphine)palladium (II) (3.51 g, 5.0 mmol). The suspension was stirred at 80° C. for 18 h, allowed to cool to room temperature and poured onto ice (400 g). The solid precipitate was filtered off, washed with water, dried in air, and the filtrate was extracted with EtOAc (300 mL), washed with water (100 mL), mixed with the solid precipitate and concentrated. The crude product was purified by chromatography [SiO2; EtOAc:toluene (0:1-1:9-2:3)] and the material with Rf 0.23 (isopropyl ether) was triturated with isohexane to give the title compound (11.1 g, 57%) as a yellow solid; mp. 133-140° C.; NMR δH (400 MHz, DMSO) 6.70 (1H, q, J 2.0 Hz), 6.95 (1H, s), 7.16 (2H, br s), 7.27 (1H, d, J 3.6 Hz) and 7.92 (1H, t, J 1.0 Hz).

後処理

  1. temperatureto cool to room temperature
  2. additionpoured onto ice (400 g)
  3. filtrationThe solid precipitate was filtered off
  4. washwashed with water
  5. customdried in air
  6. extractionthe filtrate was extracted with EtOAc (300 mL)
  7. washwashed with water (100 mL)
  8. additionmixed with the solid precipitate
  9. concentrationconcentrated
  10. customThe crude product was purified by chromatography [SiO2; EtOAc:toluene (0:1-1:9-2:3)]
  11. customthe material with Rf 0.23 (isopropyl ether) was triturated with isohexane

出典と根拠

ORDレコード
ord-b47238b752264867847b322086626272
出典データセット
uspto-grants-2011_01
特許番号
US07875600B2

反応ノート

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