Water → HCID 67061109, compound

HRID 401047Notes

Reaction equation

HRID 401047 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:14]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:17][C:16](=[O:32])[NH:15]2)[CH:7]=[C:8]([N+:11]([O-])=O)[C:9]=1[OH:10])[CH3:2].[NH4+].[Cl-].C1COCC1.O>CO.[Fe]>[NH2:11][C:8]1[CH:7]=[C:6]([CH:14]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:17][C:16](=[O:32])[NH:15]2)[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:9]=1[OH:10]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 51347325HCID 51347325, compound2×

Product 1

HCID 67061109HCID 67061109, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one (Compound 1) (431 mg, 1.0 mmol) and NH4Cl (268 mg, 5.0 mmol) in MeOH:THF:H2O=2:1:1 (8 mL) was added iron power (280 mg, 5.0 mmol) and the reaction mixture was heated to reflux for 1.0 h. The reaction mixture was cooled to room temperature and filtered. The filtered mass was washed with methanol (5.0 mL). The filtrate was concentrated in vacuo to afford 4-(3-amino-5-ethoxy-4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one as a white solid (386 mg, 96.3%), which was used directly for the next step.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1.0 h
  3. filtrationfiltered
  4. washThe filtered mass was washed with methanol (5.0 mL)
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0211066e7505410a9f2bef2897b56ac4
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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