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4-Methoxybenzylamine → 3-{3-[6-Chloro-2-(4-methoxy-benzylamino)-pyrimidin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-benzonitrile

HRID 426222
ノート
印刷プレビュー

反応式

HRID 426222 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:14]([C:15]([C:17]3[CH:18]=[C:19]([CH:22]=[C:23]([CH3:25])[CH:24]=3)[C:20]#[N:21])=[O:16])=[C:13]([CH:26]([CH3:28])[CH3:27])[C:12](=[O:29])[NH:11][C:10]2=[O:30])[CH:5]=[C:4]([Cl:31])[N:3]=1.[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1>C(#N)C>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:14]([C:15]([C:17]3[CH:18]=[C:19]([CH:22]=[C:23]([CH3:25])[CH:24]=3)[C:20]#[N:21])=[O:16])=[C:13]([CH:26]([CH3:27])[CH3:28])[C:12](=[O:29])[NH:11][C:10]2=[O:30])[CH:5]=[C:4]([NH:39][CH2:38][C:37]2[CH:40]=[CH:41][C:34]([O:33][CH3:32])=[CH:35][CH:36]=2)[N:3]=1.[Cl:31][C:4]1[N:3]=[C:2]([NH:39][CH2:38][C:37]2[CH:40]=[CH:41][C:34]([O:33][CH3:32])=[CH:35][CH:36]=2)[N:7]=[C:6]([CH2:8][N:9]2[C:14]([C:15]([C:17]3[CH:18]=[C:19]([CH:22]=[C:23]([CH3:25])[CH:24]=3)[C:20]#[N:21])=[O:16])=[C:13]([CH:26]([CH3:27])[CH3:28])[C:12](=[O:29])[NH:11][C:10]2=[O:30])[CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 754524-MethoxybenzylamineHCID 596868473-[3-(2,6-Dichloro-pyrimidin-4-ylmethyl)-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile

生成物 2

HCID 866192313-{3-[2-Chloro-6-(4-methoxy-benzylamino)-pyrimidin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-benzonitrile収率 25%
HCID 86619232
3-{3-[6-Chloro-2-(4-methoxy-benzylamino)-pyrimidin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-benzonitrile
収率 54%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 3-[3-(2,6-Dichloro-pyrimidin-4-ylmethyl)-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile (458 mg, 1 mmol) and p-methoxy benzylamine (262 μl, 2 mmol) in acetonitrile (10 ml) was refluxed for 2.5 hr. After cooling to room temperature, the mixture was evaporated in vacuo. The residue was dissolved in dichloromethane (20 ml), washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexane (1:2)) to afford 143 mg (25%) of 3-{3-[2-Chloro-6-(4-methoxy-benzylamino)-pyrimidin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-benzonitrile (Rf=0.14) and 302 mg (54%) of 3-{3-[6-Chloro-2-(4-methoxy-benzylamino)-pyrimidin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-benzonitrile (Rf=0.06) as a white solid, respectively.

後処理

  1. temperaturewas refluxed for 2.5 hr
  2. customthe mixture was evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (20 ml)
  4. washwashed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (eluent, EA:hexane (1:2))

出典と根拠

ORDレコード
ord-77b4ebd13045466580510f302326e282
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08106064B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート