Isopropanol → [2-(2,5-Dichloropyrimidin-4-ylamino)-phenoxy]acetonitrile

HRID 1687575Notes

Reaction equation

HRID 1687575 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[O:13][CH2:14][C:15]#[N:16].C(O)(C)C>>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[O:13][CH2:14][C:15]#[N:16])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 2372592,4,5-TrichloropyrimidineHCID 118049172-(2-Aminophenoxy)acetonitrile

Product 1

HCID 86633910[2-(2,5-Dichloropyrimidin-4-ylamino)-phenoxy]acetonitrileYield 53.9%

Procedure

Into an 80 ml microwave vessel was added 2,4,5-Trichloro-pyrimidine (1.86 g, 0.01 mol), (2-Amino-phenoxy)-acetonitrile (1.500 g, 0.01 mol), and N,N-DIEA (1.96 g, 0.015 mol), Isopropyl alcohol (20 mL, 0.3 mol). The reaction was microwaved at 120° C. for 60 minutes. The resulting orange suspension was filtered and the solid was washed with Isopropyl alcohol to afford a light pink solid (1.59 g, 53%). HPLC purity 95%.

Workup

  1. customThe reaction was microwaved at 120° C. for 60 minutes
  2. filtrationThe resulting orange suspension was filtered
  3. washthe solid was washed with Isopropyl alcohol

Sources & evidence

ORD record
ord-9cebb2a7ea304d8dbb2131011809b510
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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