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

HRID 76587Notes

Reaction equation

HRID 76587 reaction equation
C(N1CCN(C2C=CC([NH:20][C:21]3[C:26]([F:27])=[CH:25][N:24]=[C:23](Cl)[N:22]=3)=CC=2)CC1)C1C=CC=CC=1.[CH2:29]1[CH2:39][O:38][C:37]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][C:31]=2[O:30]1>>[CH2:29]1[CH2:39][O:38][C:37]2[CH:36]=[CH:35][C:33]([NH:34][C:23]3[N:22]=[C:21]([NH2:20])[C:26]([F:27])=[CH:25][N:24]=3)=[CH:32][C:31]=2[O:30]1

Participants

3

Reactant 2

HCID 891481,4-Benzodioxan-6-ylamineHCID 86591122N4-[4-(N-benzylpiperazino)phenyl]-2-chloro-5-fluoro-4-pyrimidineamine

Product 1

HCID 83736650N2-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamineYield 127.1%

Procedure

In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-N2-(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidineamine, the reaction of N4-[4-(N-benzylpiperazino)phenyl]-2-chloro-5-fluoro-4-pyrimidineamine (50 mg, 0.12 mmol) and 3,4-ethylenedioxyaniline (0.045 mL, 0.36 mmol) gave N4-[4-(N-benzylpiperazino)phenyl)]-N2-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine (40 mg, 63%). 1H NMR (CDCl3): δ 2.64 (t, J=4.8 Hz, 4H), 3.20 (t, J=4.8 Hz, 4H), 3.59 (s, 2H), 4.24 (m, 4H), 6.61 (d, 1H, NH), 6.68 (br, 1H, NH), 6.76 (d, J=8.7 Hz, 1H), 6.88 (dd, J=2.4 and 8.7 Hz, 1H), 6.93 (d, J=8.7 Hz, 2H), 7.19 (d, J=2.4 Hz, 1H), 7.28-7.36 (m, 5H), 7.47 (d, J=8.7 Hz, 2H), 7.87 (d, J=3.3 Hz, 1H); 19F NMR (282 MHz, CDCl3): δ−168.66; LCMS: ret. time: 18.05 min.; purity: 100%; MS (m/e): 513.10 (MH+).

Workup

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

Sources & evidence

ORD record
ord-29ce5ff7e02d49bf8efbe6a1daa0406b
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Reaction notes

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