2-chloro-5-fluoro-N-(3-hydroxyphenyl)-4-pyrimidineamine → HCID 22060338, compound

HRID 1442332Notes

Reaction equation

HRID 1442332 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.[CH2:17]([NH:19][C:20]([O:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26])=[O:21])[CH3:18]>>[CH2:17]([NH:19][C:20]([O:22][C:23]1[CH:24]=[C:25]([NH:26][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:27]=[CH:28][CH:29]=1)=[O:21])[CH3:18]

Participants

3

Reactant 2

HCID 220604512-chloro-5-fluoro-N-(3-hydroxyphenyl)-4-pyrimidineamineHCID 22060978HCID 22060978, compound

Product 1

HCID 22060338HCID 22060338, compound

Procedure

In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 3-[(N-ethylamino)carbonyloxy]aniline were reacted to provide N2-[3-[(N-ethylamino)carbonyloxy]phenyl]-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.92 (d, 1H, J=3.0 Hz), 7.67-7.55 (m, 2H), 7.24 (t, 1H, J=7.5 Hz), 7.16 (t, 1H, J=7.5 Hz), 7.07-6.98 (m, 2H), 6.84-6.79 (m, 2H), 6.67 (m, 2H), 6.60 (d, 1H, J=7.5 Hz), 5.22-5.14 (m, 1H), 3.36-3.27 (m, 2H), 2.95 (s, 1H), 2.88 (s, 1H), 1.20 (t, 3H, J=7.5 Hz); 19F NMR (282 MHz, CDCl3): −47012; LCMS: purity: 99%; MS (m/e): 384 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-4b49bd5c67d4461983b3f8b086e9a37f
Source dataset
uspto-grants-2010_02
Patent number
US07655797B2

Reaction notes

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