Dichloromethane → HCID 9943499, compound

HRID 2374201Notes

Reaction equation

HRID 2374201 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:4]=1.C(Cl)[Cl:20]>C(OCC)C>[ClH:20].[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 9943500HCID 9943500, compound

Product 1

HCID 9943499HCID 9943499, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4,6-Dimethoxy-2-(phenylethynyl)pyrimdine (320 mg, 1.3 mmol) was dissolved in CH2Cl2 (1.0 mL), and treated with HCI in diethyl ether (1.6 mL of a 1.0M solution, 1.6 mmol). A yellow solid precipitated immediately. The mixture was diluted with ethyl acetate and allowed to stand in the freezer for 16 h. The cold supernatant was decanted and the remaining solids were triturated with ethyl acetate (1.5 mL), and then hexane (3.times.2 mL). The remaining solid was dried in vacuo to afford 4,6-dimethoxy-2-(phenylethynyl)pyrimdine hydrochloride (174 mg, 47% yield) as a yellow solid. M.p. 137-138. 1H NMR (CD3OD, 300 MHz) Δ7.65-7.62 (m, 2H), 7.46-7.42 (m, 3H), 6.16 (s, 1H), 3.97 (s, 6H).

Workup

  1. customA yellow solid precipitated immediately
  2. additionThe mixture was diluted with ethyl acetate
  3. customThe cold supernatant was decanted
  4. customthe remaining solids were triturated with ethyl acetate (1.5 mL)
  5. customThe remaining solid was dried in vacuo

Sources & evidence

ORD record
ord-d56ea2a24ffc4927812963cf1edcaaf8
Source dataset
uspto-grants-2008_12
Patent number
US07462619B2

Reaction notes

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