Triethylamine → HCID 89579974、化合物

HRID 928608ノート

反応式

HRID 928608 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.Cl[C:10]1[C:11]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:19][S:18][C:12]=2[N:13]=[C:14]([CH2:16][Cl:17])[N:15]=1.C(N(CC)CC)C>C(O)C>[Cl:17][CH2:16][C:14]1[N:15]=[C:10]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]2)[C:11]2[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:19][S:18][C:12]=2[N:13]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 4207714-PiperidinemethanolHCID 23726818HCID 23726818、化合物

生成物 1

HCID 89579974HCID 89579974、化合物収率 95.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-Piperidinemethanol (0.85 g) was added to a suspension of 4-chloro-2-(chloromethyl)-5-phenyl-thieno[2,3-d]pyrimidine (1.45 g) in ethanol (70 mL). Triethylamine (1.4 mL) was added and the mixture was stirred at room temperature for 24 hr. The solvent was evaporated and the residue was dissolved in water (100 mL) and ethyl acetate (100 mL). The layers were separated and the aqueous was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (1×100 mL), dried (sodium sulfate), filtered and evaporated to give an off-white foam (1.76 g). This was purified by silica chromatography (50 g cartridge; eluent petroleum ether 40-60/ethyl acetate 0 to 50%; collection by UV trigger). Fractions corresponding to the main peak were combined and evaporated to give the target compound as a white foam (1.10 g). m/z [M+H]+373.9/375.9. Retention time 4.67 min (LCMS method+ve 6 min).

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water (100 mL)
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic layers were washed with brine (1×100 mL)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-b03b6fbd4bfa42a4b744312720d82546
出典データセット
uspto-grants-2016_03
特許番号
US09290511B2

反応ノート

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