Triethylamine → 4-[4-((R)-1-Phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzonitrile

HRID 2252765Notes

Reaction equation

HRID 2252765 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C([N:21]([CH2:24][CH3:25])CC)C>O1CCOCC1>[C:11]1([C@H:24]([NH:21][C:2]2[C:3]3[CH:10]=[C:9]([C:11]4[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=4)[NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH3:25])[CH:18]=[CH:17][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 865953354-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-benzonitrile

Product 1

HCID 573997444-[4-((R)-1-Phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 1.27 g (5 mmol) 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-benzonitrile, 1.4 ml (10 mol) triethylamine and 0.955 ml (7.5 mmol) R(+)-1-phenyl-ethylamine in 25 ml dioxane is heated under reflux for 24 h. A second portion of R(+)-1-phenyl-ethylamine (0.32 ml, 2.5 mmol) is added and heating is continued for 24 h. After addition of a third portion of R(+)-1-phenyl-ethylamine (0.32 ml, 2.5 mmol) and additional 24 h the reaction mixture is cooled to 10° C. and the title compound filtered off and washed with dioxane. From the mother liquor a second crop is obtained after concentration of the solution; m.p. 333-336° C.; MS-ES+: (M+H)+=340.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 24 h
  3. temperatureheating
  4. filtrationthe title compound filtered off
  5. washwashed with dioxane
  6. customFrom the mother liquor a second crop is obtained after concentration of the solution

Sources & evidence

ORD record
ord-3d76780609b349568caefdb87f9db220
Source dataset
uspto-grants-2008_01
Patent number
US07323469B2

Reaction notes

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