3-Aminostyrene → Trifluoroacetate

HRID 541557Notes

Reaction equation

HRID 541557 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].Cl[C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[CH2:23])[CH:17]=2)[C:12]([Cl:24])=[CH:11][N:10]=1.[CH:25]([C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30])=[CH2:26]>COCCO.Cl.C(O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:24][C:12]1[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[CH2:23])[CH:17]=2)=[N:14][C:9]([NH:30][C:29]2[CH:31]=[CH:32][CH:33]=[C:27]([CH:25]=[CH2:26])[CH:28]=2)=[N:10][CH:11]=1.[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4]

Participants

7

Reactant 2

HCID 42600413-AminostyreneHCID 866361292,5-dichloro-N-(3-vinylphenyl)pyrimidin-4-amine trifluoroacetate

Product 2

HCID 84468TrifluoroacetateYield 474%HCID 668796985-Chloro-N,N'-bis(3-vinylphenyl)pyrimidine-2,4-diamine Trifluoroacetate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 2,5-dichloro-N-(3-vinylphenyl)pyrimidin-4-amine trifluoroacetate (150 mg, 0.56 mmol) and 3-vinylaniline (200 mg, 1.0 mmol) in 2-methoxyethanol (3.8 mL) and 3 N hydrogen chloride in ethanol (0.56 mL) were mixed and heated to 150° C. for 30 minutes in a microwave. Purification by preparative LCMS (pH 2) gave the desired product as a trifluoroacetate salt (150 mg, 60%). LCMS for C20H17ClN4 (M+H)+: m/z=349.1.

Workup

  1. customPurification by preparative LCMS (pH 2)

Sources & evidence

ORD record
ord-8cee1e93a93c4a89adb37374b149650d
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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