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Potassium Carbonate → 6-(5-Chloro-2-methoxyphenyl)-2-methylpyrimidin-4-ol

HRID 28555
Notes
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Reaction equation

HRID 28555 reaction equation
C(O[C:4](=[O:17])[CH2:5][C:6]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])=O)C.Cl.[C:19]([NH2:22])(=[NH:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH3:16])=[C:8]([C:6]2[N:21]=[C:19]([CH3:20])[NH:22][C:4](=[O:17])[CH:5]=2)[CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67170Acetamidine monohydrochlorideHCID 54012347Ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate

Product 1

HCID 1363418886-(5-Chloro-2-methoxyphenyl)-2-methylpyrimidin-4-olYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(5-chloro-2-methoxy-phenyl)-3-oxopropionic acid ethyl ester (0.9 g, 3.2 mmol), acetamidine hydrochloride (448 mg, 4.7 mmol) and potassium carbonate (1.3 g, 9.6 mmol) in ethanol (15 ml) was stirred at 100° C. in thick wall tube for 60 hours. After cooling to room temperature, the mixture was poured into ice cold water. The solid was collected by filtration, washed with water and ether and dried under vacuum to provide 6-(5-chloro-2-methoxy-phenyl)-2-methyl-3H-pyrimidin-4-one (530 mg, 68% yield) as a white powder. 1H NMR (DMSO-d6) δ 2.32 (s, 3H, CH3), 3.85 (s, 3H, CH3), 6.77 (s, 1H, CH, Ar), 7.15 (d, 1H, J=8.8 Hz, Ar), 7.45 (dd, 1H, J=8.8 Hz, J=2.9 Hz, Ar), 7.90 (d, 1H, J=2.9 Hz, Ar), 12.42 (s, 1H, NH).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was poured into ice cold water
  3. filtrationThe solid was collected by filtration
  4. washwashed with water and ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5314391f367944da93370148cb759c3c
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07419984B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes