Hydrochloric Acid → HCID 178426709, compound

HRID 2243406Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:23])=[C:8]([NH:10][C:11]2[N:16]=C(C3C=NC=CC=3)C=C[N:12]=2)[CH:9]=1)([O-:3])=[O:2].CC1C=CC([N+]([O-])=O)=CC=1N.N#CN.[ClH:38]>>[ClH:38].[CH3:23][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]=1[NH:10][C:11]([NH2:16])=[NH:12]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 74442-Methyl-5-Nitroaniline

HCID 9864Cyanamide

HCID 106861492-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

Product 1

HCID 178426709HCID 178426709, compound

Procedure

In other aspects the invention provides a process for the preparation of N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine comprising: (a) reacting 2-methyl-5-nitroaniline with cyanamide in the presence of hydrochloric acid to obtain 1-(2-methyl-5-nitrophenyl)guanidine hydrochloride; (b) converting 1-(2-methyl-5-nitrophenyl)guanidine hydrochloride to 1-(2-methyl-5-nitrophenyl)guanidine nitrate; (c) condensing 3-acetylpyridine with N,N-dimethylformamide dimethyl acetal to obtain 3-(dimethylamino)-1-(3-pyridinyl)-prop-2-en-1-one; and (d) reacting 3-(dimethylamino)-1-(3-pyridinyl)-prop-2-en-1-one with 1-(2-methyl-5-nitrophenyl)guanidine nitrate to obtain N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine.

Workup

customIn other aspects the invention provides a process

Sources & evidence

ORD record: ord-1ee7d348a50343e88617a3d08e09dcad
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674901B2

Reaction notes

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