Acetic Acid → HCID 67768983, compound

HRID 1898923Notes

Reaction equation

[C:1]([C:3]([C:14](=[O:30])[N:15]([CH2:26][CH2:27][CH2:28]C)[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)=[CH:4][NH:5][C:6](=[NH:13])[N:7]1[CH2:11][CH2:10][NH:9][C:8]1=[O:12])#[N:2].O.[C:32]1(C)C=CC(S(O)(=O)=O)=C[CH:33]=1.[C:43](O)(=O)C>>[CH2:26]([N:15]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:25])[F:24])[CH:17]=1)[C:14]([C:3]1[C:1]([NH2:2])=[N:13][C:6]([N:7]2[CH2:11][CH:10]([CH:32]=[CH2:33])[NH:9][C:8]2=[O:12])=[N:5][CH:4]=1)=[O:30])[CH:27]([CH3:43])[CH3:28]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 521998p-Toluenesulfonic acid monohydrate

HCID 178449491HCID 178449491, compound

Product 1

HCID 67768983HCID 67768983, compoundYield 53.2%

Procedure

A mixture of 3.14 g (7 mmol) of a compound II (R1 =CH=CH2 ; R2, R3, R5, R6 =H; R4 =CH2CH(CH3)2), 5 ml of glacial acetic acid and 1.05 g (5.5 mmol) of p-toluenesulfonic acid monohydrate was stirred at 67°-69° for 2.5 hours and then worked up as in Example 5. 1.67 g (53.2% yield) of TLC-pure 4-amino-2-(4-vinyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-isobutyl-N-(3-trifluoromethylphenyl)amide were obtained, melting point 85°-186°.

Sources & evidence

ORD record: ord-7702f331e3ab45e794b55437a0a9497b
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571816

Reaction notes

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