Hydrochloric Acid → HCID 178517840, compound

HRID 2059852Notes

Reaction equation

HRID 2059852 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10](S(C)(=O)=O)[N:9]=2)=[CH:4][CH:3]=1.[OH-:20].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:20])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 585798714-((4-Chlorophenoxy)methyl)-2-(methylsulfonyl)pyrimidine

Product 1

HCID 178517840HCID 178517840, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-((4-Chlorophenoxy)methyl)-2-(methylsulfonyl)pyrimidine Part B (0.8 g, 2.68 mmol) was stirred in 1N NaOH (5 mL, 5.36 mmol) and THF (13 mL) at 80° C. for 30 min. The solution was cooled to RT, acidified to pH 3 using 10% aqueous HCl. The precipitated product after isolation by filtration, was washed with CH2Cl2 to afford the desired product 4-((4-chlorophenoxy)methyl)pyrimidin-2(1H)-one 6C (0.344 g, 1.45 mmol, 54% yield) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ 7.93 (1H, d, J=5.27 Hz), 7.28-7.36 (2H, m), 6.94-7.02 (2H, m), 6.10 (1H, d, J=5.27 Hz), 4.78 (2H, s).

Workup

  1. filtrationThe precipitated product after isolation by filtration
  2. washwas washed with CH2Cl2

Sources & evidence

ORD record
ord-af2f0ee36a3144aa80644d7cb293c8a9
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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