Bromoacetonitrile → [[4-Amino-2,6-bis[[(3-chloro-2-fluorophenyl)methyl]thio]-5-pyrimidinyl]amino]acetonitrile

HRID 1789943Notes

Reaction equation

HRID 1789943 reaction equation
[Cl:1][C:2]1[C:3]([F:28])=[C:4]([CH2:8][S:9][C:10]2[N:15]=[C:14]([NH2:16])[C:13]([NH2:17])=[C:12]([S:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=3[F:27])[N:11]=2)[CH:5]=[CH:6][CH:7]=1.[CH:29]([N:32](C(C)C)CC)(C)[CH3:30].BrCC#N>O1CCOCC1>[NH2:16][C:14]1[C:13]([NH:17][CH2:30][C:29]#[N:32])=[C:12]([S:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=2[F:27])[N:11]=[C:10]([S:9][CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[F:28])[N:15]=1

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 220370332,6-Bis[[(3-chloro-2-fluorophenyl)methyl]thio]-4,5-pyrimidinediamine

Product 1

HCID 22037040[[4-Amino-2,6-bis[[(3-chloro-2-fluorophenyl)methyl]thio]-5-pyrimidinyl]amino]acetonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the product of example 13, step (a) (4.2 g) and diisopropylethylamine (1.2 ml) in dioxan (40 ml) was added bromoacetonitrile (1.2 g) and the mixture heated at 100° C. for 23 hours. After cooling, the red reaction solution was adsorbed onto silica and purified by silica gel flash column chromatography, eluting with dichloromethane then 95:5 dichloromethane:ethyl acetate, to give the subtitled compound as a pale orange solid (3.1 g).

Workup

  1. temperatureAfter cooling
  2. custompurified by silica gel flash column chromatography
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-647e8eb37a8b4bd2ad684e9511d1df3d
Source dataset
uspto-grants-2006_07
Patent number
US07071193B2

Reaction notes

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