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Benzylamine → Ammonium Hydroxide

HRID 2243661
ノート
印刷プレビュー

反応式

HRID 2243661 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([S:29][CH3:30])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22](O)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:31].[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[NH4+:9].[OH-:23].[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([S:29][CH3:30])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22]([NH:39][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:31]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 7504BenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 119506223-[8-(2,6-Difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzoic acid

生成物 2

HCID 14923Ammonium Hydroxide
HCID 11950097
3-[8-(2,6-Difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(phenylmethyl)benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The compound 3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzoic acid (0.597 g, 1.35 mmol), benzyl amine (0.445 mL, 4.0 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.311 g, 1.62 mmol), 1-hydroxybenzotriazole hydrate (0.219 g, 1.62 mmol), were dissolved in CH2Cl2 (50 mL) and stirred under argon at room temperature for 16 h. The solvent was pumped off in vacuo. The reaction mixture was partitioned between ethyl acetate and water. The organic phase washed 3× with water, 1× brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude product was flash chromatographed on silica gel (25 g) eluted with a gradient of 6:1:0.1, CH2Cl2:isopropanol:NH4OH to give the title compound. Crystallization from CH2Cl2/hexane gave the title compound as a white crystalline solid. m.p. (dec)154-159° C.; LC-MS m/z 532 (M+H)+, 2.24 min (ret. time).

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic phase washed 3× with water, 1× brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customchromatographed on silica gel (25 g)
  7. washeluted with a gradient of 6:1:0.1, CH2Cl2

出典と根拠

ORDレコード
ord-5776bceccbd148a89dffac2523d22a89
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07674789B2

反応ノート

読み込み中…

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