Hydrochloric Acid → HCID 9921182, compound

HRID 1835822Notes

Reaction equation

HRID 1835822 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][CH:8]=1)[CH3:2].[ClH:17]>C(Cl)Cl.C(OCC)C>[ClH:17].[CH2:1]([C:3]1[CH:8]=[N:7][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 9921183HCID 9921183, compound

Product 1

HCID 9921182HCID 9921182, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

5-Ethyl-2-(phenylethynyl)pyrimidine (730 mg, 3.7 mmol) was dissolved in CH2Cl2 (3.0 mL) and treated with HCl in diethyl ether (4.1 mL of a 1N solution, 4.1 mmol). Upon addition of the HCl solution a solid precipitated from the solution. The mixture was diluted with diethyl ether (2 mL) and the supernatant decanted. The resultant solid was dried under high vacuum at 50° C. to afford 5-ethyl-2-(phenylethynyl)pyrimidine hydrochloride (450 mg, 49% yield) as an orange solid. M.p. 101-104° C. 1H NMR (CD3OD, 300 MHz) δ 8.75 (s, 2H), 7.58-7.55 (m, 2H), 7.41-7.32 (m, 3H), 2.67 (q, J=7.6 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H).

Workup

  1. customprecipitated from the solution
  2. additionThe mixture was diluted with diethyl ether (2 mL)
  3. customThe resultant solid was dried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-7808f6275f8547a7848751f09456f268
Source dataset
uspto-grants-2004_08
Patent number
US06774138B2

Reaction notes

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