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Ethyl 2-(4,6-dimethyl-5-nitropyrimidine-2-yloxy)acetate → Ethyl 2-(5-amino-4,6-dimethylpyrimidine-2-yloxy)acetate

HRID 1749264
Notes
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Reaction equation

HRID 1749264 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH3:11])[N:5]=[C:4]([O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:3]=1.[H][H]>C(O)C.[Pd]>[NH2:8][C:7]1[C:2]([CH3:1])=[N:3][C:4]([O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:5][C:6]=1[CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 59336196Ethyl 2-(4,6-dimethyl-5-nitropyrimidine-2-yloxy)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 59336106Ethyl 2-(5-amino-4,6-dimethylpyrimidine-2-yloxy)acetateYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

Compound 6 (75.98 g) and 5% Pd—C (7.598 g, N. E. CHEMCAT, STD Type) were suspended in ethanol (760 mL). Evacuation and replacement with hydrogen were repeated three times. Subsequently, the suspension was vigorously stirred at room temperature (20 to 30° C.) for 4.5 hours under hydrogen atmosphere. After the reaction was completed, the mixture was subjected to high precision pressure filtration (0.2 μm, PTFE) and the filtered product was washed with ethanol (474 mL). The filtrate was evaporated under reduced pressure to give 66.99 g (99.9% yield) of the desired product as a pale yellow solid.

Workup

  1. filtrationthe mixture was subjected to high precision pressure filtration (0.2 μm, PTFE)
  2. washthe filtered product was washed with ethanol (474 mL)
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3a2db42f894743cdac8d4d024dc6acc5
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09156817B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes