1,4-Benzodioxan-6-ylamine → N2-(3,4-ethylenedioxyphenyl)-5-Fluoro-N4-(1H-pyrrol-1-yl)-2,4-pyrimidinediamine

HRID 76752Notes

Reaction equation

HRID 76752 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][N:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)[C:5]([F:14])=[CH:4][N:3]=1.[CH2:15]1[CH2:25][O:24][C:23]2[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=2[O:16]1>>[CH2:15]1[CH2:25][O:24][C:23]2[CH:22]=[CH:21][C:19]([NH:20][C:2]3[N:7]=[C:6]([NH:8][N:9]4[CH:13]=[CH:12][CH:11]=[CH:10]4)[C:5]([F:14])=[CH:4][N:3]=3)=[CH:18][C:17]=2[O:16]1

Participants

3

Reactant 2

HCID 891481,4-Benzodioxan-6-ylamineHCID 220604312-chloro-5-fluoro-N-(1H-pyrrol-1-yl)-4-pyrimidineamine

Product 1

HCID 15603304N2-(3,4-ethylenedioxyphenyl)-5-Fluoro-N4-(1H-pyrrol-1-yl)-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N-(1H-pyrrol-1-yl)-4-pyrimidineamine was reacted with 3,4-ethylenedioxyaniline to produce N2-(3,4-ethylenedioxyphenyl)-5-Fluoro-N4-(1H-pyrrol-1-yl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 11.63 (s, 1H), 9.94 (s, 1H), 8.23 (d, 1H, J=4.7 Hz), 6.86 (m, 4H), 6.58 (d, 1H, J=8.8 Hz), 6.12 (t, 2H, J=2.3 Hz), 4.15 (s, 4H). LCMS: ret. time: 17.36 min.; purity: 96%; MS (m/e): 328 (MH+).

Sources & evidence

ORD record
ord-30ed29eabf2144cab666968428390cf9
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Reaction notes

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