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4,6-Dichloro-5-methylpyrimidine → 4-Chloro-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidine

HRID 1619443
Notes
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Reaction equation

HRID 1619443 reaction equation
CC(C)([O-])C.[K+].[N:7]1[CH:12]=[CH:11][CH:10]=[N:9][C:8]=1[N:13]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]1.[Cl:20][C:21]1[C:26]([CH3:27])=[C:25](Cl)[N:24]=[CH:23][N:22]=1>C1COCC1>[Cl:20][C:21]1[C:26]([CH3:27])=[C:25]([O:19][CH:16]2[CH2:15][CH2:14][N:13]([C:8]3[N:9]=[CH:10][CH:11]=[CH:12][N:7]=3)[CH2:18][CH2:17]2)[N:24]=[CH:23][N:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8188604,6-Dichloro-5-methylpyrimidineHCID 202340981-(Pyrimidin-2-yl)piperidin-4-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 866651634-Chloro-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidineYield 3.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Potassium tert-butoxide (2.86 gm, 0.01397 moles) was added to an ice-cold solution of 1-(pyrimidin-2-yl)piperidin-4-ol (2.50 gm, 0.01397 moles) and 4,6-dichloro-5-methylpyrimidine (2.27 mg, 0.01397 moles) in dry THF (15 ml) and the reaction mixture was stirred for 5 hours at 30° C. The reaction mixture was poured into ice cold water, solid precipitated was filtered and dried under vacuum to obtain 140 mg of product.

Workup

  1. additionThe reaction mixture was poured into ice cold water, solid
  2. customprecipitated
  3. filtrationwas filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-52999f5c34234070939fbe00122f346c
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772302B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes