1,4-Benzodioxan-6-ylamine → N2,N4-bis-(3,4-ethylenedioxyphenyl)-5-nitro-2,4-pyrimidinediamine

HRID 71382

Reaction equation

HRID 71382 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH2:12]1[CH2:22][O:21][C:20]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=2[O:13]1>>[CH2:12]1[CH2:22][O:21][C:20]2[CH:19]=[CH:18][C:16]([NH:17][C:2]3[N:7]=[C:6]([NH:17][C:16]4[CH:18]=[CH:19][C:20]5[O:21][CH2:22][CH2:12][O:13][C:14]=5[CH:15]=4)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=3)=[CH:15][C:14]=2[O:13]1

Participants

3

Reactant 2

HCID 891481,4-Benzodioxan-6-ylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 22060675N2,N4-bis-(3,4-ethylenedioxyphenyl)-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 3,4-ethylenedioxyaniline gave N2,N4-bis-(3,4-ethylenedioxyphenyl)-5-nitro-2,4-pyrimidinediamine. LCMS: ret. time: 30.78 min.; purity: 100%; MS (m/e): 424 (MH+); 1H NMR (CDCl3): δ 10.21 (1H, s), 9.10 (1H, s), 7.40 (1H, s), 7.11-6.71 (6H, m), 4.29 (4H, s), 4.25 (4H, s).

Workup

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

Sources & evidence

ORD record
ord-970bfe7888c64ec4858fa97389ea5ba7
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Linked notes

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