Triethylamine → HCID 51348663, compound

HRID 2177931Notes

Reaction equation

HRID 2177931 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-].CCN(CC)CC.[S:42](Cl)([CH3:45])(=[O:44])=[O:43]>CCO.[Zn].C1COCC1.O>[CH2:1]([O:3][C:4]1[C:9]([OH:10])=[C:8]([NH:11][S:42]([CH3:45])(=[O:44])=[O:43])[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]=1)[CH3:2]

Participants

9

Reactant 4

HCID 8471Triethylamine2×HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chloride2×HCID 51347325HCID 51347325, compound2×

Product 1

HCID 51348663HCID 51348663, compoundYield 21.7%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one (Compound 1) (400 mg, 0.93 mmol) was dissolved in an EtOH:H2O:THF (8 mL, 2:1:1) mixture. To this was added Zn dust (124 mg, 1.89 mmol) and NH4Cl (104 mg, 1.94 mmol) and stirred at room temperature for 18 hours. After removing a 1 mL aliquot of the reaction mixture, the remaining solution was filtered through a celite pad followed by a solvent swap to DCM/THF (2 mL/2 mL). Et3N (0.1 mL, 0.72 mmol) was added and the solution was stirred for 15 minutes. Mesyl chloride (40 μL, 0.24 mmol) was added and the solution stirred at room temperature for 18 hours. Additional Et3N (0.1 mL, 0.72 mmol) and mesyl chloride (30 μL, 0.18 mmol) was then added and stirred for an additional 6 hours. The crude mixture was concentrated in vacuo and purified by silica-gel column chromatography (0-5% MeOH in EtOAc) to afford 25 mg of Compound 75 as a faint yellow solid. 1H NMR (CD3OD 300 MHz): δ 7.25 (m, 5H), 7.16 (d, 1H), 7.03 (d, 1H), 7.01 (d, 2H), 6.89 (m, 2H), 6.84 (d, 1H), 5.19 (s, 1H), 4.62 (s, 1H), 4.10 (q, 2H), 2.87 (s, 3H), 1.40 (t, 3H); MS (ESI): m/z 480.23 [M+1]+.

Workup

  1. customAfter removing a 1 mL aliquot of the reaction mixture
  2. filtrationthe remaining solution was filtered through a celite pad
  3. stirringthe solution was stirred for 15 minutes
  4. stirringthe solution stirred at room temperature for 18 hours
  5. stirringstirred for an additional 6 hours
  6. concentrationThe crude mixture was concentrated in vacuo
  7. custompurified by silica-gel column chromatography (0-5% MeOH in EtOAc)

Sources & evidence

ORD record
ord-00abd80d1694419a864e10eea0f34251
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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