Benzylamine → N2,N4-bis(benzyl)-5-fluoro-2,4-pyrimidinediamine

HRID 71394Notes

Reaction equation

OC1C=C(N[C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18](O)[CH:17]=3)[C:12]([F:23])=[CH:11][N:10]=2)C=CC=1.Cl[C:25]1N=C(Cl)C(F)=CN=1.[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:33]([NH:40][C:9]1[N:14]=[C:13]([NH:15][CH2:16][C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:25]=2)[C:12]([F:23])=[CH:11][N:10]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

Reactant 3

HCID 7504Benzylamine

HCID 2507052,4-Dichloro-5-fluoropyrimidine

HCID 9904854R-112

Product 1

HCID 22060544N2,N4-bis(benzyl)-5-fluoro-2,4-pyrimidinediamine

Procedure

In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and benzylamine were reacted to yield N2,N4-bis(benzyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.69 (bs, 1H), 7.35-7.24 (m, 10H), 5.63 (bs, 1H), 5.27 (bs, 1H), 4.61 (d, 2H, J=6.0 Hz), 4.55 (d, 2H, J=6.0 Hz); 19F NMR (CDCl3): −48580; LCMS: ret. time: 23.73 min.; purity: 100%; MS (m/e): 309 (MH+).

Workup

customwere reacted

Sources & evidence

ORD record: ord-8d01ba469ba84516aec6e60efb63b0fa
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822685B2

Reaction notes

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