Diethyl 2-Propynylmalonate → 2-Amino-5-(prop-2-yn-1-yl)pyrimidine-4,6-diol

HRID 1153942Notes

Reaction equation

HRID 1153942 reaction equation
[C:1]([CH:6]([CH2:12][C:13]#[CH:14])[C:7](OCC)=[O:8])(OCC)=[O:2].C(=O)(O)O.[NH2:19][C:20]([NH2:22])=[NH:21]>C(O)C>[NH2:21][C:20]1[NH:22][C:1](=[O:2])[C:6]([CH2:12][C:13]#[CH:14])=[C:7]([OH:8])[N:19]=1

Participants

4

Reactant 2

HCID 28835Diethyl 2-PropynylmalonateHCID 286947Carbonic acid-guanidine (1:1)

Product 1

HCID 133694462-Amino-5-(prop-2-yn-1-yl)pyrimidine-4,6-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.0 g ethyl 2-carboethoxy-4-pentynoate [J. Org. Chem. 40, 851 (1975)] and 2.5 g of guanidine carbonate was heated to reflux in 50 ml of absolute ethanol for 24 hours. The suspension was then cooled to 20° and the solid product was collected. This was subsequently dissolved in 30 ml of water and acidified to pH 3 with 1N hydrochloric acid whereupon a thick precipitate formed. The mixture was warmed briefly to produce a filterable suspension which was then cooled, filtered and rinsed with water, then acetone. The yield of 2-amino-6-hydroxy-5-(2-propynyl)-4(3H)-pyrimidinone was 1.3 g (32%) as a slightly pink powder, m.p. 292°-293° dec. An NMR spectrum (60 MHz) in trifluoroacetic acid solution exhibited absorptions at 2.2 (1H), and 3.6 (2H) indicating the title compound.

Workup

  1. temperaturewas heated
  2. temperatureThe suspension was then cooled to 20°
  3. customthe solid product was collected
  4. dissolutionThis was subsequently dissolved in 30 ml of water
  5. customformed
  6. temperatureThe mixture was warmed briefly
  7. customto produce a filterable suspension which
  8. temperaturewas then cooled
  9. filtrationfiltered
  10. washrinsed with water

Sources & evidence

ORD record
ord-8f3dba78c4194524b3216aa3a066cb93
Source dataset
uspto-grants-1984_12
Patent number
US04487626

Reaction notes

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