Sodium Carbonate → HCID 68727548, compound

HRID 2067866Notes

Reaction equation

HRID 2067866 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[CH:20][C:19]([Br:22])=[CH:18][N:17]=2)=[CH:11][CH:10]=1)(=O)=O.[NH:23]1[CH2:32][CH2:31][CH:26]([C:27]([O:29][CH3:30])=[O:28])[CH2:25][CH2:24]1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Br:22][C:19]1[CH:20]=[N:21][C:16]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:23]3[CH2:32][CH2:31][CH:26]([C:27]([O:29][CH3:30])=[O:28])[CH2:25][CH2:24]3)=[CH:14][CH:13]=2)=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 424914Methyl isonipecotateHCID 86660115HCID 86660115, compound

Product 1

HCID 68727548HCID 68727548, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-(4-(5-Bromopyrimidin-2-ylamino)phenoxy)ethyl methanesulfonate 11 (1.55 mmol) and methyl isonipecotate (3.10 mmol) are dissolved in DMF (5 mL) and stirred at 90° C. for 12 h. After the reaction is completed, 2M Na2CO3 (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-(2-(4-(5-bromopyrimidin-2-ylamino)phenoxy)ethyl)piperidine-4-carboxylate 12. MS (m/z) (M+1)+: 435.1, 437.1.

Workup

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

Sources & evidence

ORD record
ord-fa1b8bbe73b54f11911c0d927a0167d3
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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