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Sodium Carbonate → Methyl 1-(4-(5-bromopyrimidin-2-ylamino)phenethyl)piperidine-4-carboxylate

HRID 2067871
Notes
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Reaction equation

HRID 2067871 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=2)=[CH:10][CH:9]=1)(=O)=O.[NH:22]1[CH2:31][CH2:30][CH:25]([C:26]([O:28][CH3:29])=[O:27])[CH2:24][CH2:23]1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Br:21][C:18]1[CH:17]=[N:16][C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][N:22]3[CH2:31][CH2:30][CH:25]([C:26]([O:28][CH3:29])=[O:27])[CH2:24][CH2:23]3)=[CH:9][CH:10]=2)=[N:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 424914Methyl isonipecotateHCID 866601174-(5-Bromopyrimidin-2-ylamino)phenethyl methanesulfonate

Product 1

HCID 68727496Methyl 1-(4-(5-bromopyrimidin-2-ylamino)phenethyl)piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

The reaction mixture of 4-(5-bromopyrimidin-2-ylamino)phenethyl methanesulfonate 19 (1.55 mmol) and methyl isonipecotate (3.10 mmol) in DMF (5 mL) is stirred at 90° C. for 12 h. After the reaction is complete, Na2CO3 (2.0 M, 20 mL) is added and the resulting mixture is extracted with EtOAc (50 mL). The organic layer is separated and concentrated to give crude methyl 1-(4-(5-bromopyrimidin-2-ylamino)phenethyl)piperidine-4-carboxylate 20. MS (m/z) (M+1)+: 419.1.

Workup

  1. extractionthe resulting mixture is extracted with EtOAc (50 mL)
  2. customThe organic layer is separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f1f3a2ad8ea641c3b91a9144dbcd469b
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08293757B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes