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

HRID 1153942ノート

反応式

HRID 1153942 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8f3dba78c4194524b3216aa3a066cb93
出典データセット
uspto-grants-1984_12
特許番号
US04487626

反応ノート

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