Allyl bromide → N-[4-(2-Propenyloxy)phenyl]-4-(3-pyridinyl)-2-pyrimidinamine

HRID 2352178Notes

Reaction equation

HRID 2352178 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[N:8]=2)[CH:2]=1.[H-].[Na+].[CH2:23](Br)[CH:24]=[CH2:25]>CN(C)C=O>[CH2:25]([O:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:9]2[N:8]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:12]=[CH:11][N:10]=2)=[CH:15][CH:16]=1)[CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 143471904-[[4-(3-Pyridinyl)-2-pyrimidinyl]amino]phenol

Product 1

HCID 14347192N-[4-(2-Propenyloxy)phenyl]-4-(3-pyridinyl)-2-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 2.73 g portion of dry 4-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenol was dissolved in 50 ml of dry dimethylformamide. A 528 mg portion of sodium hydride (50% in oil) was added, the reaction was sealed and stirred for 45 minutes. A solution of 1.33 g of allyl bromide in 10 ml of dimethylformamide was added, the sealed mixture was stirred overnight and then evaporated at 80° C. The residue was partitioned between water and chloroform. The organic phase was separated, dried and filtered. The filtrate was evaporated and the residue crystallized from chloroform-hexane, giving 1.7 g of the desired product as yellow crystals, mp 105°-108° C.

Workup

  1. customthe reaction was sealed
  2. stirringthe sealed mixture was stirred overnight
  3. customevaporated at 80° C
  4. customThe residue was partitioned between water and chloroform
  5. customThe organic phase was separated
  6. customdried
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. customthe residue crystallized from chloroform-hexane

Sources & evidence

ORD record
ord-845d8e2d306a43bfa690bc130108c6a5
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

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