Oxalic Acid → (+/-)-1-[3-[[(3,4-Dihydro-2h-1-benzopyran-2-yl)-methyl]amino]propyl]tetrahydro-2(1h)-pyrimidinethione ethanedioate

HRID 367279ノート

反応式

HRID 367279 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH:11]=O.[NH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][NH:19][C:18]1=[S:23].[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>CO.[Pd]>[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH2:11][NH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][NH:19][C:18]1=[S:23]

参加物

6

反応物 3

HCID 971Oxalic Acid2 回HCID 20627851HCID 20627851、化合物HCID 225732481-(3-aminopropyl)tetrahydro-2(1H)-pyrimidinethione

生成物 1

HCID 22573245(+/-)-1-[3-[[(3,4-Dihydro-2h-1-benzopyran-2-yl)-methyl]amino]propyl]tetrahydro-2(1h)-pyrimidinethione ethanedioate収率 7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A mixture of 3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde (0.015 mol) and 1-(3-aminopropyl)tetrahydro-2(1H)-pyrimidinethione (0.01 mol) in methanol (150 ml) was hydrogenated for 2 days at room temperature (atmospheric pressure) with palladium on activated carbon (2 g) as a catalyst. After uptake of H2 (1 eq.), the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 95/5). The pure fractions were collected and the solvent was evaporated. The residue (0.3 g) was dissolved in ethanol (30 ml) and converted into the ethanedioic acid salt (1:1) with ethanedioic acid (0.3 g; 0.0124 mol). The precipitate was filtered off and dried (vacuum), yielding 0.3 g (7%) of (±)-1-[3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]amino]propyl]tetrahydro-2(1H)-pyrimidinethione ethanedioate (1:1); mp. 217.6° C. (comp. 14).

後処理

  1. filtrationAfter uptake of H2 (1 eq.), the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 95/5)
  4. customThe pure fractions were collected
  5. customthe solvent was evaporated
  6. dissolutionThe residue (0.3 g) was dissolved in ethanol (30 ml)
  7. filtrationThe precipitate was filtered off
  8. customdried (vacuum)

出典と根拠

ORDレコード
ord-88c04fd772d54c129ed4f6304c362adb
出典データセット
uspto-grants-2000_10
特許番号
US06133277

反応ノート

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