tert-Butanol → HCID 13369448, compound

HRID 1153943Notes

Reaction equation

HRID 1153943 reaction equation
[C:1]([OH:5])(C)([CH3:3])[CH3:2].[Cl:6][C:7]1[C:12](CC#C)=[C:11](Cl)[N:10]=[C:9]([NH2:17])[N:8]=1.[OH-].[Na+]>O>[Cl:6][C:7]1[C:12]2[CH:2]=[C:1]([CH3:3])[O:5][C:11]=2[N:10]=[C:9]([NH2:17])[N:8]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 13369447HCID 13369447, compound

Product 1

HCID 13369448HCID 13369448, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 80 ml t-butanol and 60 ml water was added 6.0 g of 4,6-dichloro-5-(2-propynyl)-2-pyrimidinamine followed by 30 ml of 2N sodium hydroxide. After heating to reflux (ca 70°) for 20 hours, the mixture was cooled and the solid product was collected by filtration. The yield of product was 1.8 g, m.p. 255°-257°. An NMR (60 MHz) spectrum in trifluoroacetic acid solution exhibited absorptions at 2.8 (doublet) and 6.6 (triplet) ppm in a 3 to 1 ratio indicating the title compound.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux (ca 70°) for 20 hours
  3. temperaturethe mixture was cooled
  4. filtrationthe solid product was collected by filtration

Sources & evidence

ORD record
ord-60779cddbd324280a47ceb4a63fcbf08
Source dataset
uspto-grants-1984_12
Patent number
US04487626

Reaction notes

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