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

HRID 1749264Notes

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]

Participants

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

filtrationthe mixture was subjected to high precision pressure filtration (0.2 μm, PTFE)
washthe filtered product was washed with ethanol (474 mL)
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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