3-Benzyloxyaniline → N2,N4-bis(3-benzyloxyphenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 226640

Reaction equation

HRID 226640 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[CH2:10]([O:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([O:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[N:7]=[C:6]([NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[C:18]([O:17][CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:19]=3)[C:5]([F:9])=[CH:4][N:3]=2)[CH:22]=[CH:23][CH:24]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 928923-BenzyloxyanilineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 22060851N2,N4-bis(3-benzyloxyphenyl)-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 3-benzyloxyaniline were reacted to yield N2,N4-bis(3-benzyloxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.98 (bs, 1H), 7.42–6.99 (m, 16H), 6.75 (d, 1H, J=2.4 Hz), 6.71 (m, 1H), 6.60 (dd, 1H, J=2.4 and 8.4 Hz), 6.32 (m, 1H), 4.97 (s, 2H), 4.94 (s, 2H); LCMS: ret. time: 32.56 min.; purity: 98%; MS (m/e): 493 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-cf8936327d284bb7873fbfe11a9bbc24
Source dataset
uspto-grants-2009_07
Patent number
US07557210B2

Linked notes

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