Nitric Acid → HCID 178503569, compound

HRID 550846

Reaction equation

HRID 550846 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[N+:11]([O-])([OH:13])=[O:12]>>[OH:1][C:2]1[C:7]([N+:11]([O-:13])=[O:12])=[C:6]([OH:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 178503559HCID 178503559, compound

Product 1

HCID 178503569HCID 178503569, compoundYield 72%

Conditions

Temperature
0 °C

Procedure

Step1: 4,6-Dihydroxy-2-methylthiopyrimidine (10.0 g, 63.22 mmol) was added over 1 hr to fuming nitric acid (30 mL) at 0° C. The red solution was stirred an additional 1 hr at 0° C. and then poured onto ice to give a light brown solid which was filtered off and washed with water and diethyl ether. The solid was dried under vacuo to give 4,6-Dihydroxy-2-methylthio-5-nitropyrimidine (9.30 g, 72%) as a light brown solid. LRMS for C5H5N3O4S (M+H)+ at m/z=203. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. additionpoured onto ice
  2. customto give a light brown solid which
  3. filtrationwas filtered off
  4. washwashed with water and diethyl ether
  5. customThe solid was dried under vacuo

Sources & evidence

ORD record
ord-6daaf9205bb04b09ac2d14e08e931837
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Linked notes

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