2,4-Dichloro-5-nitropyrimidine → N2,N4-bis-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-nitro-2,4-pyrimidinediamine

HRID 405380

Reaction equation

HRID 405380 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[F:12][C:13]1([F:23])[O:17][C:16]2[CH:18]=[CH:19][C:20]([NH2:22])=[CH:21][C:15]=2[O:14]1>>[F:23][C:13]1([F:12])[O:17][C:16]2[CH:18]=[CH:19][C:20]([NH:22][C:2]3[N:7]=[C:6]([NH:22][C:20]4[CH:19]=[CH:18][C:16]5[O:17][C:13]([F:23])([F:12])[O:14][C:15]=5[CH:21]=4)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=3)=[CH:21][C:15]=2[O:14]1

Participants

3

Reactant 2

HCID 5212662,4-Dichloro-5-nitropyrimidineHCID 27368935-Amino-2,2-difluoro-1,3-benzodioxole

Product 1

HCID 22060509N2,N4-bis-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-nitro-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of 2,4-dichloro-5-nitropyrimidine with 2,2-difluoro-5-amino-1,3-benzodioxole gave N2,N4-bis-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-nitro-2,4-pyrimidinediamine. LCMS: ret. time: 38.15 min.; purity: 96%; MS (m/e): 467 (M+); 1H NMR (CDCl3): δ 10.76 (1H, s), 10.49 (1H, s), 9.20 (1H, s), 7.74 (2H, s), 7.56 (1H, d, J=11.4 Hz), 7.33 (2H, m), 7.20 (1H, m).

Workup

  1. customIn like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine

Sources & evidence

ORD record
ord-620629b2cb7e468bbdeefd9fc49ce919
Source dataset
uspto-grants-2014_06
Patent number
US08748597B2

Linked notes

Loading…