2,4-Dichloro-5-fluoropyrimidine → HCID 22060371, compound

HRID 1753468Notes

Reaction equation

HRID 1753468 reaction equation
C1COC2C=CC(NC3C(F)=CN=C(NC4C=CC=C(O)C=4)N=3)=CC=2O1.[NH2:27][C:28]1[CH:33]=[C:32]([CH3:34])[C:31]([OH:35])=[C:30]([Cl:36])[CH:29]=1.[Cl:37][C:38]1[N:43]=[C:42](Cl)[C:41]([F:45])=[CH:40][N:39]=1>>[Cl:37][C:38]1[N:43]=[C:42]([NH:27][C:28]2[CH:33]=[C:32]([CH3:34])[C:31]([OH:35])=[C:30]([Cl:36])[CH:29]=2)[C:41]([F:45])=[CH:40][N:39]=1

Participants

4

Reactant 3

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 27744394-Amino-2-chloro-6-methylphenolHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamine

Product 1

HCID 22060371HCID 22060371, compound

Procedure

In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 4-amino-2-chloro-6-methylphenol and 2,4-dichloro-5-fluoropyrimidine resulted 2-chloro-N4-(3-chloro-4-hydroxy-5-methylphenyl)-5-fluoro-4-pyrimidineamine. The reaction of 2-chloro-N4-(3-chloro-4-hydroxy-5-methylphenyl)-5-fluoro-4-pyrimidineamine and 3-methoxycarbonylmethyleneoxyaniline (1.95 g, 11 mmol) gave N4-(3-chloro-4-hydroxy-5-methylphenyl)-5-fluoro-N2-(3-methoxycarbonylmethyleneoxyphenyl)-2,4-pyrimidinediamine (850 mg, 55%). 1H NMR (CD3OD): δ 2.22 (s, 3H), 3.76 (s, 3H), 4.52 (s, 2H), 6.50 (dt, J=2.7 and 6.3 Hz, 1H), 7.09-7.14 (m, 2H), 7.24 (t, J=1.8 Hz, 1H), 7.30 (t, J=1.2 Hz, 1H), 7.49 (d, J=2.4 Hz, 1H), 7.88 (d, J=3.9 Hz, 1H); 19F NMR (282 MHz, CD3OD): δ−168.70; LCMS: ret. time: 20.63 min.; purity: 98.56%; MS (m/e): 432.96 (MH+).

Sources & evidence

ORD record
ord-5716b3de619b435d8577e226400cf522
Source dataset
uspto-grants-2015_10
Patent number
US09162989B2

Reaction notes

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