Sodium Hydroxide → HCID 13924019, compound

HRID 1789283Notes

Reaction equation

HRID 1789283 reaction equation
[NH2:1][C:2]1[NH:7][C:6]([C:9]#[C:10]C(O)C)(C)[CH:5]=[CH:4][N:3]=1.[OH-].[Na+].O1CCOC[CH2:17]1>C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([C:9]#[CH:10])[CH:5]=[C:4]([CH3:17])[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 178467710HCID 178467710, compound

Product 1

HCID 13924019HCID 13924019, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4.44 g of 4-(2-amino-4-methylpyrimidin-4-yl)-3-butyne-2-ol, 1 g of sodium hydroxide, 5 ml of dioxane and 50 ml of toluene was refluxed for two hours. The toluene layer was decanted from the residue, concentrated under reduced pressure and chromatographed on a silica gel dry column. The product band eluted with (2:3:0.05) ethyl acetate/dichloromethane/THF. Extraction with THF and concentration of the solvent gave 0.75 g of the title compound as a solid, 129°-130° dec.; IR(nujol) 2119(w, C≡C) cm-1 ; PMR(60 MHz, CDCl3) δ2,3(s, CH3, 3H), 3.1(s, C≡CH, 1H), 5.3-5.6(bs, NH2, 2H), 6.6(s, Het-H, 1H).

Workup

  1. temperaturewas refluxed for two hours
  2. customThe toluene layer was decanted from the residue
  3. concentrationconcentrated under reduced pressure
  4. customchromatographed on a silica gel
  5. customdry column
  6. washThe product band eluted with (2:3:0.05) ethyl acetate/dichloromethane/THF
  7. extractionExtraction with THF and concentration of the solvent

Sources & evidence

ORD record
ord-bc4fd103bc7e48e291eff8e257739a7b
Source dataset
uspto-grants-1987_08
Patent number
US04689069

Reaction notes

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