Thionyl Chloride → 4-Amino-5-(4-chloro-2-methoxy-benzoylamino)-pyrimidine

HRID 1155068Notes

Reaction equation

HRID 1155068 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.ClC1C=CC(C(O)=O)=C(OC)C=1.S(Cl)(Cl)=O.Cl.Cl.[NH2:31][C:32]1[C:37]([NH2:38])=[CH:36][N:35]=[CH:34][N:33]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[NH2:31][C:32]1[C:37]([NH:38][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=2[O:11][CH3:12])=[CH:36][N:35]=[CH:34][N:33]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 936824-Chloro-o-anisic acidHCID 20562693Pyrimidine-4,5-diamine dihydrochlorideHCID 221424504-Chloro-2-methoxybenzoyl chloride

Product 1

HCID 205627114-Amino-5-(4-chloro-2-methoxy-benzoylamino)-pyrimidine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

The 4-chloro-2-methoxy-benzoyl chloride prepared from 5.6 g of 4-chloro-2-methoxy-benzoic acid and 100 ml of thionyl chloride was dissolved as crude product in 100 ml of pyridine and mixed successively with 5 g of 4,5-diaminopyrimidine dihydrochloride and 1 g of 4-dimethylamino pyridine. After stirring for at first 2 hours at room termperature and then for 1.5 hours at 100° C., the reaction mixture was evaporated to dryness, mixed with water, and neutralized with sodium bicarbonate. The precipitate obtained was used in the next step without further purification.

Workup

  1. waitfor 1.5 hours at 100° C.
  2. customthe reaction mixture was evaporated to dryness
  3. additionmixed with water
  4. customThe precipitate obtained
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-f1c433141f824c62825e2d1e77af32cb
Source dataset
uspto-grants-1981_11
Patent number
US04299834

Reaction notes

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