5-Fluoropyrimidine-2,4-diamine → HCID 86600718, compound

HRID 733934Notes

Reaction equation

HRID 733934 reaction equation
[F:1][C:2]1[C:3]([NH2:9])=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.ClC1N=C(N[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)C(F)=CN=1>>[F:1][C:2]1[C:3]([NH:9][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 2556085-Fluoropyrimidine-2,4-diamineHCID 220604512-chloro-5-fluoro-N-(3-hydroxyphenyl)-4-pyrimidineamine

Product 1

HCID 86600718HCID 86600718, compoundYield 41%

Procedure

In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-N2-(3-hydroxyphenyl))-5-fluoro-2,4-pyrimidinediamine, 4-(aminocarbonylmethyleneoxy)aniline (198 mg, 1.2 mmol) and 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine (95 mg, 0.4 mmol) gave N2-[4-aminocarbonylmethyleneoxy)phenyl]-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine (60 mg, 41%). 1H NMR (CD3OD): δ 4.55 (s, 2H), 6.75 (dm, J=7.5 Hz, 1H), 7.08 (d, J=9.3 Hz, 2H), 7.18 (m, 2H), 7.22 (d, J=8.7 Hz, 1H), 7.46 (d, J=9.0 Hz, 2H), 8.09 (d, 1H); LCMS: ret. time: 14.38 min.; purity: 100%; MS (m/e): 370.00 (MH+).

Sources & evidence

ORD record
ord-ca371744b7de49d889b13fc915546cbd
Source dataset
uspto-grants-2009_09
Patent number
US07589200B2

Reaction notes

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