Sodium hydride → HCID 15767101, compound

HRID 375086Notes

Reaction equation

HRID 375086 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13]#[N:14])=[CH:6][CH:5]=1.Br[C:22]1[CH:23]=[N:24][CH:25]=[N:26][CH:27]=1>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:22]2[CH:23]=[N:24][CH:25]=[N:26][CH:27]=2)[C:13]#[N:14])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 783445-BromopyrimidineHCID 13953402HCID 13953402, compound

Product 1

HCID 15767101HCID 15767101, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a 250 ml. 3 neck round bottomed flask under nitrogen was charged 1.2 g of 60% NaH (1.5 eq., 0.0293 moles), washed 2 times with 15 ml. hexanes, in 40 ml. DMF. Dropwise was added 5.0 g. of 4-(4-chlorophenyl)-2-phenylbutanenitrile (1.0 eq., 0.0195 moles) in 10 ml. of DMF and was stirred for one hour at rt. This was followed by the addition of 4.67 g. of 5-bromopyrimidine (1.5 eq., 0.0293 moles) in 10 ml. of DMF to the reaction mixture which resulted in an exotherm to 35° C. After 45 min. GLC analysis showed no unreacted nitrile. The reaction was quenched by the addition of 100 ml. Water and then extracted with 250 ml. EtOAc. The organic phase Was washed with 2 times 100 ml. water, dried over MgSO4 and concentrated to give 7.3 g. of oil. 6.0 g. of crude product was purified by flash chromatography with 3:7 EtOAc/hexane to give 2.3 g. of a white solid mp. 89°-91° C. (43.1% based on chromatographic portion).

Workup

  1. washwashed 2 times with 15 ml
  2. additionDropwise was added 5.0 g
  3. additionThis was followed by the addition of 4.67 g
  4. customThe reaction was quenched by the addition of 100 ml
  5. extractionWater and then extracted with 250 ml
  6. washThe organic phase Was washed with 2 times 100 ml
  7. dry with materialwater, dried over MgSO4
  8. concentrationconcentrated
  9. customto give 7.3 g
  10. customof crude product was purified by flash chromatography with 3:7 EtOAc/hexane
  11. customto give 2.3 g

Sources & evidence

ORD record
ord-693f2893729d47b194c283e9c33fef7c
Source dataset
uspto-grants-1996_01
Patent number
US05484787

Reaction notes

Loading…