HCID 68510049, compound → HCID 59198061, compound

HRID 2195721Notes

Reaction equation

HRID 2195721 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1)=O.[N+]([O-])(O)=O.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=1[NH:30][C:31]([NH2:33])=[NH:32]>>[CH3:14][O:13][C:11]1[CH:12]=[C:7]([C:5]2[CH:4]=[CH:3][N:33]=[C:31]([NH:30][C:22]3[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=[CH:26][C:21]=3[CH3:20])[N:32]=2)[CH:8]=[N:9][CH:10]=1

Participants

3

Reactant 2

HCID 68510049HCID 68510049, compoundHCID 178426711HCID 178426711, compound

Product 1

HCID 59198061HCID 59198061, compound

Procedure

Condensation of 12 with N-(2-methyl-5-nitro-phenyl)-guanidine nitrate 2 using a similar procedure for the preparation of 4 affords 4-(5-methoxypyridin-3-yl)-N-(2-methyl-5-nitrophenyl)pyrimidin-2-amine 13. 1H NMR (400 MHz, d6-DMSO) δ 9.23 (s, 1H), 8.93 (d, J=1.2 Hz, 1H), 8.80 (d, J=2.0 Hz, 1H), 8.63 (d, J=5.2 Hz, 1H), 8.44 (d, J=2.8 Hz, 1H), 8.00 (s, 1H), 7.91 (dd, J=2.0, 8.4 Hz, 1H), 7.62 (d, J=5.2 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 3.90 (s, 3H), 2.44 (s, 3H). MS (m/z) (M+1)+: 338.1

Workup

  1. customfor the preparation of 4

Sources & evidence

ORD record
ord-2e74e595c2a1486c869e42af9de51f90
Source dataset
uspto-grants-2012_12
Patent number
US08338417B2

Reaction notes

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