Water → HCID 67061109, compound

HRID 924833Notes

Reaction equation

HRID 924833 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-45d6cf222a8845bbb898ead5267d3744
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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