N-[3-(1,1,2,2-tetrafluoro-ethoxy)phenyl]-4-(2-cyano-4-pyridyl)-2-pyrimidineamine → N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(2-aminomethyl-4-pyridyl)-2-pyrimidineamine

HRID 976280Notes

Reaction equation

HRID 976280 reaction equation
[F:1][C:2]([F:28])([O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([C:26]#[N:27])[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].[H-].C([Al+]CC(C)C)C(C)C.C1COCC1>CO>[F:28][C:2]([F:1])([O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([CH2:26][NH2:27])[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4]

Participants

4

Reactant 2

HCID 19967016N-[3-(1,1,2,2-tetrafluoro-ethoxy)phenyl]-4-(2-cyano-4-pyridyl)-2-pyrimidineamineHCID 86597605diisobutylaluminium hydride THF

Product 1

HCID 19966992N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(2-aminomethyl-4-pyridyl)-2-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg (0.26 mmol) of N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(2-cyano-4-pyridyl)-2-pyrimidineamine and 1.28 ml (1.0M in THF, 1.28 mmol) of diisobutylaluminium hydride/THF solution are stirred for 1 h at -20°. After the addition of 2 ml of methanol, the reaction mixture is heated to RT and the reaction product is isolated by filtration. After concentration under reduced pressure using a rotovapor and chromatography [methylene chloride:methanol:ammonia (conc.)=95:5:]N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(2-aminomethyl-4-pyridyl)-2-pyrimidineamine is obtained; m.p. 64°-67°, FAB-MS: 394 (M+ +H).

Workup

  1. customthe reaction product is isolated by filtration
  2. concentrationAfter concentration under reduced pressure

Sources & evidence

ORD record
ord-b1bd9faea7774b148706b99cb3762eac
Source dataset
uspto-grants-1997_03
Patent number
US05612340

Reaction notes

Loading…