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4,4'-(6-Chloropyrimidine-2,4-diyl)dimorpholine → 3-(2,6-Dimorpholinopyrimidin-4-yl)-4-methylaniline

HRID 594056
ノート
印刷プレビュー

反応式

HRID 594056 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:3]=1.[CH3:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=1B1OC(C)(C)C(C)(C)O1>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[O:11]1[CH2:12][CH2:13][N:8]([C:6]2[N:7]=[C:2]([C:22]3[CH:23]=[C:24]([CH:26]=[CH:27][C:21]=3[CH3:20])[NH2:25])[CH:3]=[C:4]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:5]=2)[CH2:9][CH2:10]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 6863344,4'-(6-Chloropyrimidine-2,4-diyl)dimorpholineHCID 160860894-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

生成物 1

HCID 904083603-(2,6-Dimorpholinopyrimidin-4-yl)-4-methylaniline収率 96%

試薬・触媒・溶媒 3

HCID 178418807HCID 178418807、化合物触媒HCID 80711,2-Dimethoxyethane
溶媒
HCID 10340Sodium Carbonate溶媒

反応条件

温度
120 °C

実験手順

To a solution of 4,4′-(6-chloropyrimidine-2,4-diyl)dimorpholine (1.0 equiv.) and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.5 equiv.) in DME and 2M sodium carbonate (3:1, 0.2 M) was added PdCl2(dppf)-DCM adduct (0.100 equiv.) in a microwave vial equipped with a stir bar. The reaction was heated to 120° C. for 20 min in the microwave. The reaction mixture qas quenched with water and the aqueous layer was separated and extracted with EtOAc (×3). The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The material was purified via silica gel column chromatography eluting with 100% DCM to 10% MeOH/DCM to afford 3-(2,6-dimorpholinopyrimidin-4-yl)-4-methylaniline in 96% yield. LCMS (m/z) (M+H)=356.2, Rt=0.44 min.

後処理

  1. customvial equipped with a stir bar
  2. customThe reaction mixture qas quenched with water
  3. customthe aqueous layer was separated
  4. extractionextracted with EtOAc (×3)
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe material was purified via silica gel column chromatography
  9. washeluting with 100% DCM to 10% MeOH/DCM

出典と根拠

ORDレコード
ord-1709db82e8004ff6a5843968a7288ae2
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242969B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート