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

HRID 2067871Notes

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

Participants

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

extractionthe resulting mixture is extracted with EtOAc (50 mL)
customThe organic layer is separated
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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