Triethylamine → HCID 66826244, compound

HRID 2177932Notes

Reaction equation

HRID 2177932 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([CH:11]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:14][C:13](=[O:29])[NH:12]2)=[CH:4][C:3]=1[O:30][CH3:31].[NH4+].[Cl-].CCN(CC)CC.[S:41](Cl)([CH3:44])(=[O:43])=[O:42]>CCO.[Zn].C1COCC1.O>[OH:1][C:2]1[C:3]([O:30][CH3:31])=[CH:4][C:5]([CH:11]2[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:14][C:13](=[O:29])[NH:12]2)=[CH:6][C:7]=1[NH:8][S:41]([CH3:44])(=[O:43])=[O:42]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 51347475HCID 51347475, compound2×

Product 1

HCID 66826244HCID 66826244, compoundYield 9%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Hydroxy-3-methoxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one (Compound 9) (100 mg, 0.24 mmol) was dissolved in an EtOH:H2O:THF (4 mL, 2:1:1) mixture. To this was added Zn dust (26 mg, 0.40 mmol) and NH4Cl (26 mg, 0.48 mmol) and stirred at room temperature for 1 day, followed by stirring at 50° C. for 1 day. The solution was filtered through a celite pad followed by a solvent swap to DCM (5 mL). Excess Et3N (0.1 ml, 0.72 mmol) was added and stirred for 15 minutes, followed by excess addition of mesyl chloride (50 μL, 0.3 mmol) and stirring over night. The crude mixture was directly purified by silica-gel column chromatography (0 to 5% MeOH in EtOAc) to yield 10 mg of Compound 76 as a faint yellow solid. 1H NMR (CD3OD 300 MHz): δ 7.27 (m, 5H), 7.06 (m, 1H), 7.04 (d, 2H), 6.91 (m, 2H), 6.61 (d, 1H), 6.38 (d, 1H), 5.51 (s, 1H), 5.14 (s, 1H), 3.77 (s, 3H)); MS (ESI): m/z 466.17 [M+1]+.

Workup

  1. stirringby stirring at 50° C. for 1 day
  2. filtrationThe solution was filtered through a celite pad
  3. stirringstirred for 15 minutes
  4. stirringstirring over night
  5. customThe crude mixture was directly purified by silica-gel column chromatography (0 to 5% MeOH in EtOAc)

Sources & evidence

ORD record
ord-c3d7d50be1f84498beed2c3afffa58cb
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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