Water → HCID 178429496, compound

HRID 629973Notes

Reaction equation

HRID 629973 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[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.O.[NH4+].[Cl-]>C(O)C.[Fe]>[NH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[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

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 178429455HCID 178429455, compound

Product 1

HCID 178429496HCID 178429496, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a suspension of the 2-{[(2-chloro-6-nitrophenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (1.0 g, 3.20 mmol) in ethanol (30 mL), a water mixture of iron powder (1.07 g, 19.24 mmol) and equivalent NH4Cl (0.741 g, 9.6 mmol) was added. The reaction mixture was stirred at room temperature for 48 hours. The reaction mixture was filtered over Celite and washed with methanol, and the solvent was evaporated. The precipitated solid was filtered off and washed with ether to provide the titled amine (0.316 g, 35% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 4.42 (s, 2H), 6.01 (bs, 1H), 6.60 (m, 2H), 6.95 (t, J=8.0, 16.1 Hz, 1H); M+282.06.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered over Celite
  3. washwashed with methanol
  4. customthe solvent was evaporated
  5. filtrationThe precipitated solid was filtered off
  6. washwashed with ether

Sources & evidence

ORD record
ord-31ecd81e2d00419f968bd7b28594248a
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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