Hydrochloric Acid → HCID 135900179, compound

HRID 884641Notes

Reaction equation

HRID 884641 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([C:12]2[CH:32]=[CH:31][C:15]([O:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[CH:14][C:13]=2[CH3:33])=O)=[CH:4][C:3]=1[CH3:34].Cl.[NH2:36][C:37]([NH2:39])=[O:38]>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:12]3[CH:32]=[CH:31][C:15]([O:16][CH2:17][CH:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]4)=[CH:14][C:13]=3[CH3:33])[NH:39][C:37](=[O:38])[N:36]=2)=[CH:4][C:3]=1[CH3:34]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1176UreaHCID 68596887HCID 68596887, compound

Product 1

HCID 135900179HCID 135900179, compoundYield 7%

Conditions

Temperature
110 °C

Procedure

To a sealed pressure vessel was added (E)-tert-butyl 4-((4-(3-(4-hydroxy-3-methylphenyl)acryloyl)-3-methylphenoxy)methyl)piperidine-1-carboxylate (100 mg, 0.215 mmol), 4N HCl in dioxanes (2.0 mL), and urea (64 mg, 1.07 mmol). The pressure vessel was sealed and heated to 110° C. overnight. The reaction was then cooled to rt, concentrated via rotary evaporation and purified via preparatory HPLC (5-85% AmAc) to give 4-(4-hydroxy-3-methylphenyl)-6-(2-methyl-4-(piperidin-4-ylmethoxy)phenyl)pyrimidin-2(1H)-one (6.0 mg, 7% yield).

Workup

  1. customThe pressure vessel was sealed
  2. temperatureThe reaction was then cooled to rt
  3. concentrationconcentrated via rotary evaporation
  4. custompurified via preparatory HPLC (5-85% AmAc)

Sources & evidence

ORD record
ord-542da6d32e60422ea1eb9129104b9943
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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