Ammonia → Aminocyclopyrachlor-methyl

HRID 2282939Notes

Reaction equation

HRID 2282939 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]([OH:13])=[O:12])[C:3]=1[Cl:14].S(Cl)(Cl)=O.O.N.[CH3:21]O>S(=O)(=O)(O)O>[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]([O:13][CH3:21])=[O:12])[C:3]=1[Cl:14]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 887MethanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 17747875Aminocyclopyrachlor2×

Product 1

HCID 16725794Aminocyclopyrachlor-methyl

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
5 °C

Procedure

To a solution of 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (i.e. the product of Step D1 or D2 of Example 2) (2.0 g, 8.5 mmol) in methanol (20 mL) was added dropwise thionyl chloride (4 mL, 70 mmol). The mixture was heated at reflux for 24 h. Concentrated sulfuric acid (5 drops) was added, and the reaction mixture was heated at reflux for 16 h. After the mixture was cooled, water (30 mL) was added, and aqueous ammonia (28%, 10 mL) was added dropwise. The mixture was cooled to 5° C., and the solid was isolated by filtration, washed with water and dried in a vacuum oven at 40° C. to afford the title product (2.3 g), a compound of the present invention.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 16 h
  5. temperatureAfter the mixture was cooled
  6. customthe solid was isolated by filtration
  7. washwashed with water
  8. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-cced96e1119f402aaf0c6c7cd2490f91
Source dataset
uspto-grants-2015_09
Patent number
US09144240B2

Reaction notes

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