3-(4-Aminophenoxy)-1,2-propanediol → HCID 22061139, compound

HRID 1783047Notes

Reaction equation

HRID 1783047 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[C:5]([F:16])=[CH:4][N:3]=1.[OH:17][CH:18]([CH2:28][OH:29])[CH2:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>>[OH:17][CH:18]([CH2:28][OH:29])[CH2:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=3)[C:5]([F:16])=[CH:4][N:3]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 4592603-(4-Aminophenoxy)-1,2-propanediolHCID 220604512-chloro-5-fluoro-N-(3-hydroxyphenyl)-4-pyrimidineamine

Product 1

HCID 22061139HCID 22061139, compound

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-(3-hydroxyphenyl)-4-pyrimidineamine and 4-(2,3-dihydroxypropoxy)aniline were reacted to produce N2-[4-(2,3-dihydroxypropoxy)phenyl]-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.38 (s, 1H), 9.18 (s, 1H), 8.98 (s, 1H), 8.12 (d, 1H, J=3.5 Hz), 7.58 (d, 2H, J=8.8 Hz), 7.22 (d, 1H, J=2.3 Hz), 7.12 (dd, 2H, J=2.3 and 8.8 Hz), 6.79 (d, 2H, J=8.8 Hz), 6.45 (d, 1H, J=8.8 Hz), 4.91 (d, 1H, J=5.3 Hz), 4.65 (t, 1H, J=5.8 Hz), 3.92-3.89 (m, 1H), 3.79-3.74 (m, 2H), 3.44 (t, 2H, J=5.3 Hz); LCMS: ret. time: 12.79 min.; purity: 89%; MS (m/e): 387 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-25789d6d20634be7990dd2b067ea892e
Source dataset
uspto-grants-2009_03
Patent number
US07498435B2

Reaction notes

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