2,4-Dichloro-5-nitropyrimidine → HCID 11789809, compound

HRID 1661121Notes

Reaction equation

HRID 1661121 reaction equation
ClC1N=C(Cl)C([N+]([O-])=O)=CN=1.[N+:12]([NH:15][C@H:16]([C:24]([OH:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-])=O>[Pd]>[NH2:12][NH:15][C@H:16]([C:24]([OH:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 5212662,4-Dichloro-5-nitropyrimidineHCID 22863191HCID 22863191, compound

Product 1

HCID 11789809HCID 11789809, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2,4-dichloro-5-nitropyrimidine is first coupled to a nitrophenylalanine derivative and the product is allowed to react with a dialkylamine, either directly or utilizing “Buchwald” palladium catalyzed coupling conditions. The resulting product is then hydrogenated yielding an aminophenylalanine derivative. This is coupled to 2-chloro-3-nitropyridine followed by reduction of the nitro group. Cyclization with CDI followed by alkylation with methyl iodide or other alkylating agent gives the imidazolone. Reduction of the pyrimidine nitro group followed by the introduction of the N-isopropyl group through reductive amination followed by sulfonylation with a sulfonyl chloride (or alternatively acylation with an acid chloride) gives the ester. Hydrolysis with formic acid affords the product.

Sources & evidence

ORD record
ord-e66b331e48034d06ae145a3ee1466b88
Source dataset
uspto-grants-2011_10
Patent number
US08030328B2

Reaction notes

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