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Lithium Chloride → 2,4-Dichloro-6-(1-hydroxymethyl-cyclopropoxy)-pyrimidin-5-ol

HRID 528468
Notes
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Reaction equation

HRID 528468 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2([CH2:12][OH:13])[CH2:11][CH2:10]2)[C:5]([O:14]C)=[C:4]([Cl:16])[N:3]=1.[Cl-].[Li+]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([Cl:16])[C:5]([OH:14])=[C:6]([O:8][C:9]2([CH2:12][OH:13])[CH2:10][CH2:11]2)[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 86711751[1-(2,6-Dichloro-5-methoxy-pyrimidin-4-yloxy)-cyclopropyl]-methanol

Product 1

HCID 867117522,4-Dichloro-6-(1-hydroxymethyl-cyclopropoxy)-pyrimidin-5-olYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of [1-(2,6-dichloro-5-methoxy-pyrimidin-4-yloxy)-cyclopropyl]-methanol (800 mg, 3.02 mmol) and lithium chloride (600 mg, 14.15 mmol) in anhydrous DMF (3 mL) was heated at 140° C. for 10 minutes using microwave irradiation, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, gradient 0-5% methanol in DCM) affording 2,4-Dichloro-6-(1-hydroxymethyl-cyclopropoxy)-pyrimidin-5-ol (300 mg, 40%). LCMS: RT=2.52 min, [M−H]−=249/251/253.

Workup

  1. custommicrowave irradiation
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by column chromatography (SiO2, gradient 0-5% methanol in DCM)

Sources & evidence

ORD record
ord-7697ceb72fe14d2896cb4452b5b77449
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346817B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes