tert-Butyl bromoacetate → N4-(3-aminophenyl)-N2-(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 1932054Notes

Reaction equation

HRID 1932054 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=3)[C:12]([F:23])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>>[NH2:22][C:18]1[CH:17]=[C:16]([NH:15][C:13]2[C:12]([F:23])=[CH:11][N:10]=[C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([N:1]=[CH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:3]=3)[N:14]=2)[CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 10215022N2,N4-bis(3-aminophenyl)-5-fluoro-2,4-primidinediamine

Product 1

HCID 22060994N4-(3-aminophenyl)-N2-(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of N2,N4-bis(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine, N2,N4-bis(3-aminophenyl)-5-fluoro-2,4-pyrimidinediamine and tert-butyl bromoacetate were reacted together to give N4-(3-aminophenyl)-N2-(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 18.33 min.; purity: 94.5%; MS (m/e): 369.09 (MH+).

Workup

  1. customwere reacted together

Sources & evidence

ORD record
ord-a5bfb1bdd4464c358931478fc225885b
Source dataset
uspto-grants-2012_05
Patent number
US08188276B2

Reaction notes

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