Ammonia → HCID 86689331, compound

HRID 1504933Notes

Reaction equation

HRID 1504933 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([O:13][CH3:14])=[C:4](Cl)[N:3]=1.[NH3:16]>CS(C)=O.O>[NH2:16][C:4]1[N:3]=[C:2]([Cl:1])[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]=1[O:13][CH3:14]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 866893322,4-Dichloro-6-(2-furanyl)-5-methoxypyrimidine

Product 1

HCID 86689331HCID 86689331, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2,6-Dichloro-5-methoxy-4-furan-2-ylpyrimidine (500 mg, 2.0 mmol) (see Example 5 for the preparation of 2,6-dicholor-5-methoxy-4-furan-2-yl pyrimidine) was dissolved in dry DMSO (10 mL) and heated to 60° C. This mixture was treated with a gentle stream of ammonia. After approximately 2 h, conversion was complete to about a 95:5 ratio of mono-amino isomers (having a molar weight of 225 g/mol). This mixture was cooled and diluted with water (50 mL), and the product extracted with ethyl acetate (2×50 mL). Then, the product was washed with ethyl acetate, twice with water (25 mL), and once with saturated sodium chloride (25 mL). The result was dried and concentrated. The product was purified by column chromatography using silica with a 5 to 20% ramp of ethyl acetate/hexane to give the title compound (400 mg, 89% yield). The various isomers were not separated.

Workup

  1. temperatureThis mixture was cooled
  2. extractionthe product extracted with ethyl acetate (2×50 mL)
  3. washThen, the product was washed with ethyl acetate, twice with water (25 mL)
  4. customThe result was dried
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-30dd758acec24cdeaacdcc627e80d53e
Source dataset
uspto-grants-2015_12
Patent number
US09216958B2

Reaction notes

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