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

HRID 594056

반응식

HRID 594056 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1709db82e8004ff6a5843968a7288ae2
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242969B2

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