HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium hydride → 4,6-Bis-(1,1-dimethylethyl)-5-[(2-methoxyethoxy) methoxy]-2-pyrimidine carboxylic acid methyl ester

HRID 326676
Notes
Print preview

Reaction equation

HRID 326676 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[N:6]=1)=[O:4].[H-].[Na+].[CH3:22][O:23][CH2:24][CH2:25][O:26][CH2:27]Cl>C1COCC1.O.[NH4+].[Cl-]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]([O:15][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[N:10]=1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 152753194,6-Bis (1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester

Product 1

HCID 540881314,6-Bis-(1,1-dimethylethyl)-5-[(2-methoxyethoxy) methoxy]-2-pyrimidine carboxylic acid methyl esterYield 100%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent2×
HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4,6-bis-(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester (4.0 g, 15.0 mmoles) in 50 mL of THF is added to a suspension of NaH (0.39 g, 16.5 mmoles) in THF (50 mL) at 0° C. When addition is complete, the reaction mixture is stirred at 0° C. for 15 minutes. 2-methoxyethoxymethyl chloride (2.0 g, 16.5 mmoles) is added and the solution is warmed to room temperature. The reaction mixture is stirred at room temperature overnight. It is diluted with 100 mL H2O and 100 mL of saturated aqueous NH4Cl. The layers are separated, and the aqueous phase is washed with Et2O (3×100 mL). The combined organic phases are washed with 100 mL brine and dried over MgSO4. Evaporation of Et2O gives 5.3 g (100%) of the desired ester as an oil.

Workup

  1. additionWhen addition
  2. temperaturethe solution is warmed to room temperature
  3. stirringThe reaction mixture is stirred at room temperature overnight
  4. customThe layers are separated
  5. washthe aqueous phase is washed with Et2O (3×100 mL)
  6. washThe combined organic phases are washed with 100 mL brine
  7. dry with materialdried over MgSO4
  8. customEvaporation of Et2O

Sources & evidence

ORD record
ord-3eb83e9ade39460080ea1786972bca87
Source dataset
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05270319

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes