Chloromethyl Methyl Ether → HCID 18315823, compound

HRID 275967Notes

Reaction equation

HRID 275967 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([N:15]3[CH2:24][CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]3[CH3:25])[CH:12]=[C:11]([CH3:26])[N:10]=2)=[CH:4][CH:3]=1.[CH3:27][O:28][CH2:29][Cl:30]>C(OCC)C>[ClH:30].[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([N:15]3[CH2:24][CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]3[CH3:25])[C:12]([CH2:27][O:28][CH3:29])=[C:11]([CH3:26])[N:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 18315741HCID 18315741, compound

Product 1

HCID 18315823HCID 18315823, compoundYield 0.05%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

2-(4-Fluorophenylamino)-6-methyl-4-(1-methyl-1,2,3,4-tetrahydroisoquino-line-2-yl)pyrimidine (0.9 g, 2.58 mmol) was added to chloromethyl methyl ether (3 ml) in a sealed tube. The mixture was stirred at 80° C. for 1 day. After cooling to room temperature, ethyl ether was added to mixture. Resulting solid was removed by filtration. Filtrate was washed with aqueous 2N NaOH solution, dried over sodium sulfate, and concentrated under reduced pressure. Crude product was purified with a silica gel column chromatography (eluent: ethyl acttate:hexane=1:3). Purified compound was treated with HCl solution in ethyl ether. Precipitated solid was isolated by filtration, washed with ethyl ether, and dried in vacuum. It gave 0.6 mg of the titled compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. customResulting solid
  3. customwas removed by filtration
  4. washFiltrate was washed with aqueous 2N NaOH solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customCrude product was purified with a silica gel column chromatography (eluent: ethyl acttate:hexane=1:3)
  8. additionPurified compound was treated with HCl solution in ethyl ether
  9. customPrecipitated solid
  10. customwas isolated by filtration
  11. washwashed with ethyl ether
  12. customdried in vacuum

Sources & evidence

ORD record
ord-976615a521d04ca3a1ffe6d6eaf00cca
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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