Triethylamine → 2-[(2-chloro-3-nitrophenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

HRID 576945

Reaction equation

HRID 576945 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(N(CC)CC)C.Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:20]=1[Cl:28]>C(O)C>[Cl:28][C:20]1[C:21]([N+:25]([O-:27])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][S:8][C:6]1[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 183630451-(Bromomethyl)-2-chloro-3-nitrobenzeneHCID 178429541HCID 178429541, compound

Product 1

HCID 1784294392-[(2-chloro-3-nitrophenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-oneYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (200 mg, 1.4 mmol) was dissolved in absolute ethanol (15 mL), then triethylamine (230 μL, 1.7 mmol) and 1-(bromomethyl)-2-chloro-3-nitrobenzene (350 mg, 1.4 mmol) were added. The mixture was stirred overnight at room temperature. The solid was filtered, washed with methanol, and then dried in vacuo to afford 2-{[(2-chloro-3-nitrophenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as white solid (277 mg, 64% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.23 (s, 3H), 4.56 (s, 2H), 6.00 (bs, 1H), 7.56 (t, J=7.9 Hz, 1H), 7.95 (d, J=8.2 Hz, 2H); LRMS (ES+) m/z 312 (100%, M+1), 314 (45%, M+3).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with methanol
  3. customdried in vacuo

Sources & evidence

ORD record
ord-cfceb032ac2344e1a95b94f1266a0035
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Linked notes

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