Allylamine → N2-allyl-5-bromo-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine

HRID 1474919Notes

Reaction equation

HRID 1474919 reaction equation
C1CO[C:8]2[CH:7]=[CH:6][C:5]([NH:11][C:12]3[C:17](F)=[CH:16][N:15]=[C:14]([NH:19][C:20]4C=CC=[C:22](O)[CH:21]=4)[N:13]=3)=[CH:4][C:3]=2[O:2]1.[Br:27]C1C(NC2C=CC=C(O)C=2)=NC(Cl)=NC=1.C(N)C=C>>[CH2:20]([NH:19][C:14]1[N:13]=[C:12]([NH:11][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([OH:2])[CH:4]=2)[C:17]([Br:27])=[CH:16][N:15]=1)[CH:21]=[CH2:22]

Participants

4

Reactant 3

HCID 7853AllylamineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamineHCID 22060529HCID 22060529, compound

Product 1

HCID 22061004N2-allyl-5-bromo-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine

Procedure

In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 5-bromo-2-chloro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and allylamine were reacted to yield N2-allyl-5-bromo-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 8.08 (s, 1H), 7.21 (t, 1H, J=8.1 Hz), 7.02-6.97 (m, 2H), 6.71 (dd, 1H, J=2.4 and 8.7 Hz), 5.91-5.77 (m, 1H), 5.19-5.09 (m, 2H), 3.94-3.89 (m, 2H); LCMS: ret. time: 18.33 min.; purity: 99%; MS (m/e): 322 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-487c081e388c4836808a7c520974d5cb
Source dataset
uspto-grants-2015_04
Patent number
US09018204B1

Reaction notes

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