Acetic Acid → HCID 59258907, compound

HRID 641692Notes

Reaction equation

HRID 641692 reaction equation
[CH:1]1([NH:6][C:7]2[C:12]([CH:13]=O)=[C:11]([CH3:15])[N:10]=[C:9]([S:16][CH3:17])[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1CCCCC1.CC(O)=O.[CH2:28]([O:30][C:31](=[O:38])[CH2:32][C:33](OCC)=[O:34])[CH3:29]>>[CH2:28]([O:30][C:31]([C:32]1[C:33](=[O:34])[N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:7]2[N:8]=[C:9]([S:16][CH3:17])[N:10]=[C:11]([CH3:15])[C:12]=2[CH:13]=1)=[O:38])[CH3:29]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 86619624HCID 86619624, compound

Product 1

HCID 59258907HCID 59258907, compoundYield 39.4%

Procedure

A solution of 4-cyclopentylamino-6-methyl-2-methylsulfanyl-pyrimidine-5-carbaldehyde (20.8 g, 0.083 mol), piperidine (8.2 mL) and AcOH (9.4 mL) in malonic acid diethyl ester (150 mL) was stirred at 130° C. for 72 hours. TLC (petroleum ether/EtOAc 4:1) indicated about half of the starting material was consumed. The reaction mixture was then concentrated in vacuo and the residue was purified by column chromatography (silica gel, petroleum ether/EtOAc 4:1) to yield the title compound (11.3 g, 39.4%) as a yellow solid.

Workup

  1. customwas consumed
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customthe residue was purified by column chromatography (silica gel, petroleum ether/EtOAc 4:1)

Sources & evidence

ORD record
ord-8582671405664ea9ae0020caea490822
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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