Hydrochloric Acid → HCID 178481601, compound

HRID 33964

Reaction equation

HRID 33964 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)=[C:5]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[N:4]=[C:3]1SC.C(Cl)Cl.C[OH:31].Cl>O1CCOCC1.[OH-].[Na+]>[OH:31][C:3]1[N:2]([CH3:1])[C:7](=[O:8])[C:6]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)=[C:5]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[N:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226129Dichloromethane methanolHCID 223466413-methyl-2-methylsulfanyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Product 1

HCID 178481601HCID 178481601, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 3-methyl-2-methylsulfanyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (10.1 g, 28.1 mmol) was heated to 100° C. in 100 mL 1,4-dioxane and 60 mL 2.5M sodium hydroxide. After 7 h, TLC (95:5 DCM/MeOH) shows the solution to have no remaining starting material. The reaction was cooled to room temperature and acidified to pH 5 with 5M HCl. The resulting precipitate was collected by filtration, and then suspended in 100 mL hot methanol. The solid was cooled to room temperature then collected by filtration and washed with 100 mL diethylether. The product was air dried overnight to give a pale yellow solid. M+1=330.2.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. temperatureThe solid was cooled to room temperature
  3. filtrationthen collected by filtration
  4. washwashed with 100 mL diethylether
  5. customdried overnight
  6. customto give a pale yellow solid

Sources & evidence

ORD record
ord-4dcf350333074a329c3813bb192a0da1
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Linked notes

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