2,4-Dichloro-5-fluoropyrimidine → N2,N4-bis(coumarin-7-yl)-5-fluoro-2,4-pyrimidinediamine

HRID 1163593Notes

Reaction equation

HRID 1163593 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](COC)=[CH:16][C:17](=[O:21])[O:18]2)=[CH:13][CH:12]=1>>[O:18]1[C:19]2[C:14](=[CH:13][CH:12]=[C:11]([NH:10][C:2]3[N:7]=[C:6]([NH:10][C:11]4[CH:20]=[C:19]5[C:14]([CH:15]=[CH:16][C:17](=[O:21])[O:18]5)=[CH:13][CH:12]=4)[C:5]([F:9])=[CH:4][N:3]=3)[CH:20]=2)[CH:15]=[CH:16][C:17]1=[O:21]

Participants

3

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 5194427-Amino-4-(methoxymethyl)-2H-chromen-2-one

Product 1

HCID 22060887N2,N4-bis(coumarin-7-yl)-5-fluoro-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 7-amino-4-methoxymethylcoumarin were reacted to yield N2,N4-bis(coumarin-7-yl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10.38 (s, 1H), 8.42 (d, 1H, J=3 Hz), 8.28 (m, 1H), 8.05-7.93 (m, 2H), 7.77-7.50 (m, 4H), 6.31 (s, 1H), 6.29 (s, 1H), 4.66 (s, 2H), 4.65 (s, 2H), 3.43 (s, 3H), 3.41 (s, 3H); LCMS: MS (m/e): 505 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-00e2cc02cb7844eeac2014f04cc47916
Source dataset
uspto-grants-2010_10
Patent number
US07820819B2

Reaction notes

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