Pyridine → N2,N4-Bis(3-acetyloxyphenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 71370Notes

Reaction equation

HRID 71370 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7](C2N=C(N)N=C(N)C=2F)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[OH:20][C:21]1[CH:22]=[C:23]([NH:27][C:28]2[N:33]=[C:32]([NH:34]C3C=CC=C(O)C=3)[C:31]([F:42])=[CH:30][N:29]=2)[CH:24]=[CH:25][CH:26]=1.[C:43](Cl)(=[O:45])[CH3:44].N1C=CC=CC=1>C(Cl)Cl>[C:43]([O:20][C:21]1[CH:22]=[C:23]([NH:27][C:28]2[N:33]=[C:32]([NH:34][C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=3)[C:31]([F:42])=[CH:30][N:29]=2)[CH:24]=[CH:25][CH:26]=1)(=[O:45])[CH3:44]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 9904854R-112HCID 86596593(3-Acetoxyphenyl]-5-fluoro-2,4-pyrimidinediamine

Product 1

HCID 22060567N2,N4-Bis(3-acetyloxyphenyl)-5-fluoro-2,4-pyrimidinediamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-acetoxyaniline were reacted to yield N2,N4-bis[(3-acetoxyphenyl]-5-fluoro-2,4-pyrimidinediamine. Alternatively, N2,N4-bis[(3-acetoxyphenyl]-5-fluoro-2,4-pyrimidinediamine can be prepared by acetylation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine with acetyl chloride in the presence of pyridine in CH2Cl2. 1H NMR (CDCl3): δ 8.00 (bs, 1H), 7.51-7.25 (m, 8H), 2.32 (s, 3H), 2.28 (s, 3H); LCMS: ret. time: 22.14 min; purity: 100%; MS (m/e): 397 (MH+).

Sources & evidence

ORD record
ord-6b2c079f91664d498159ccae0a547fd0
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Reaction notes

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