Dichloromethane → HCID 178429448, compound

HRID 577034Notes

Reaction equation

HRID 577034 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][S:12][C:13]1[N:18]=[C:17]([OH:19])[CH:16]=[C:15]([CH3:20])[N:14]=1.[NH4+].[Cl-].C(Cl)Cl>C(Cl)Cl.CCO.O.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:11][S:12][C:13]2[N:18]=[C:17]([OH:19])[CH:16]=[C:15]([CH3:20])[N:14]=2)=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 178429452HCID 178429452, compound

Product 1

HCID 178429448HCID 178429448, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 86647907HCID 86647907, compoundSolvent

Procedure

2-{[(2-chloro-4-nitrophenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (282 mg, 1.0 mmol) was dissolved in DCM/EtOH/H2O (20 mL/20 mL/10 mL). Iron (550 mg, 10 mmol) and NH4Cl (540 mg, 10 mmol) were added. The mixture was stirred at room temperature for 3 hours. DCM (200 mL) was added to extract the product. The organic phase was dried over MgSO4 and evaporated. The crude product was purified by CombiFlash (0 to 8% MeOH/DCM) to provide the title compound as a yellow solid (100 mg, 35% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.22 (s, 3H), 4.37 (s, 2H), 5.95 (br, 1H), 6.65 (d, 1H), 6.92 (s, 1H), 7.38 (d, 1H); M+ 282.

Workup

  1. extractionto extract the product
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated
  4. customThe crude product was purified by CombiFlash (0 to 8% MeOH/DCM)

Sources & evidence

ORD record
ord-2d1ed61580fd4f389ddd5368e2f8f379
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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