Chloromethyl Methyl Ether → HCID 22599711, compound

HRID 1592198Notes

Reaction equation

HRID 1592198 reaction equation
[H-].[Na+].[CH2:3]([O:7][C:8]1[N:13]=[CH:12][N:11]=[C:10]([CH:14]([OH:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)[C:4]#[C:5][CH3:6].[CH3:22][O:23][CH2:24]Cl.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:8]1[N:13]=[CH:12][N:11]=[C:10]([CH:14]([O:21][CH2:22][O:23][CH3:24])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:9]=1)[C:4]#[C:5][CH3:6]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22599869HCID 22599869, compound

Product 1

HCID 22599711HCID 22599711, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 1.5 ml of tetrahydrofuran was suspended 0.05 g of sodium hydride (60% in oil), to which 0.2 g of 6-(2-butynyloxy)-4-(α-hydroxybenzyl)pyrimidine was added under ice cooling, followed by stirring for 15 minutes. Then, 0.2 ml of a tetrahydrofuran solution containing 0.08 g of chloromethyl methyl ether was slowly added dropwise, followed by further stirring at the same temperature for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.25 g of 6-(2-butynyloxy)-4-(α-methoxymethoxybenzyl)pyrimidine (the present compound (137)).

Workup

  1. additionwas slowly added dropwise
  2. stirringby further stirring at the same temperature for 2 hours
  3. extractionextracted three times with chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-084c6ee86b7a451596eb54cf25c9a3a5
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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