Ammonium Hydroxide → HCID 9859347, compound

HRID 1975232Notes

Reaction equation

HRID 1975232 reaction equation
[NH2:1][C:2]1[O:3][C:4]([C:11](=O)[C:12]([CH3:15])([CH3:14])[CH3:13])=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:6]=1.[OH-].[NH4+:18]>C(O)(C)(C)C>[NH2:1][C:2]1[N:18]=[C:11]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:4]([OH:3])=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:6]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 19101100HCID 19101100, compound

Product 1

HCID 9859347HCID 9859347, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 1-[2-amino-4-(1,1-dimethylethyl)-5-oxazolyl]-2,2-dimethyl-l-propanone (15 g) in t-butanol (80 mL) and concentrated ammonium hydroxide (80 mL) is heated at 180° C. for 60 hours in a steel bomb. The reaction mixture is cooled and concentrated to half its volume on the rotovap. The product is extracted into ether (3×250 mL). The ether extract is dried (MgSO4) and evaporated. The residue is purified by flash chromatography (silica, 20% EtOAc/hexane) to give pure 2-amino-4,6-bis(1,1-dimethylethyl)-5-hydroxypyrimidine (4.5 g, 34%) which crystallizes from cold hexane; mp 92°-93° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated to half its volume on the rotovap
  3. extractionThe product is extracted into ether (3×250 mL)
  4. extractionThe ether extract
  5. dry with materialis dried (MgSO4)
  6. customevaporated
  7. customThe residue is purified by flash chromatography (silica, 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-9c4cf0fa6782403483ca89b042725df8
Source dataset
uspto-grants-1994_02
Patent number
US05284949

Reaction notes

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