Cesium carbonate → (R)-7-(4-morpholinophenyl)-N-((4-(pyrimidin-2-yl)morpholin-2-yl)methyl)pyrido[4,3-b]pyrazin-5-amine

HRID 57647

Reaction equation

HRID 57647 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][C@H:3]([CH2:7][NH:8][C:9]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:21][CH:20]=3)[N:10]=2)[CH2:2]1.Br[C:32]1[N:37]=[CH:36][CH:35]=[CH:34][N:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[O:28]1[CH2:29][CH2:30][N:25]([C:22]2[CH:21]=[CH:20][C:19]([C:11]3[N:10]=[C:9]([NH:8][CH2:7][C@H:3]4[O:4][CH2:5][CH2:6][N:1]([C:32]5[N:37]=[CH:36][CH:35]=[CH:34][N:33]=5)[CH2:2]4)[C:18]4[C:13](=[N:14][CH:15]=[CH:16][N:17]=4)[CH:12]=3)=[CH:24][CH:23]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 783452-BromopyrimidineHCID 71113404(S)-N-(morpholin-2-ylmethyl)-7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-amine

Product 1

HCID 71113950(R)-7-(4-morpholinophenyl)-N-((4-(pyrimidin-2-yl)morpholin-2-yl)methyl)pyrido[4,3-b]pyrazin-5-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)—N-(morpholin-2-ylmethyl)-7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-amine (100 mg, 0.246 mmol), 2-bromopyrimidine (59 mg, 0.37 mmol) and cesiumcarbonate (193 mg, 0.592 mmol) in DMF (2 mL) was heated at 100° C. in a sealed tube for overnight. Then the mixture was extracted with EA, washed with brine, concentrated and purified by flash column chromatography, eluting with DCM/MeOH to give product as light yellow solid. MS (m/z): 485 (M+H)+

Workup

  1. extractionThen the mixture was extracted with EA
  2. washwashed with brine
  3. concentrationconcentrated
  4. custompurified by flash column chromatography
  5. washeluting with DCM/MeOH
  6. customto give product as light yellow solid

Sources & evidence

ORD record
ord-ef64dc99c85f443da08f1a0eda8e388a
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

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