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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
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HRID 426222 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 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-benzonitrile수율 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
수율 54%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-77b4ebd13045466580510f302326e282
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08106064B2

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