Hydrochloric Acid → HCID 9943499, compound

HRID 902083Notes

Reaction equation

HRID 902083 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.[ClH:19]>C(Cl)Cl.C(OCC)C>[ClH:19].[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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9943500HCID 9943500, compound

Product 1

HCID 9943499HCID 9943499, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

4,6-Dimethoxy-2-(phenylethynyl)pyrimdine (320 mg, 1.3 mmol) was dissolved in CH2Cl2 (1.0 mL), and treated with HCl 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-155f0cbfa7b043a5b6e3e8c4aec8990d
Source dataset
uspto-grants-2008_04
Patent number
US07365074B2

Reaction notes

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