4-Chloroaniline → 5-chloro-N-(4-chlorophenyl)-2-fluoro-6-morpholin-4-ylpyrimidin-4-amine

HRID 1245419Notes

Reaction equation

HRID 1245419 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Cl:9][C:10]1[C:11]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[N:12][C:13]([F:17])=[N:14][C:15]=1F.C(N(CC)C(C)C)(C)C>O1CCOCC1.C(O)(C)C>[Cl:9][C:10]1[C:15]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:14][C:13]([F:17])=[N:12][C:11]=1[N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 21912455HCID 21912455, compound

Product 1

HCID 219124595-chloro-N-(4-chlorophenyl)-2-fluoro-6-morpholin-4-ylpyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

4-Chloroaniline (1.44 g) was added to a solution of the product from step (i) (0.88 g) and N,N-diisopropylethylamine (0.484 g) in 1,4-dioxane (15 ml) and isopropylalcohol (15 ml) and the mixture heated at 110° C. for 6 days. The mixture was partitioned between ethyl acetate and water, the organics dried (MgSO4), and evaporated under reduced pressure. The solid was triturated with ethyl acetate, filtered and the filtrate purified by chromatography on silica eluting with 3% ethyl acetate in toluene. Yield 0.28 g

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialthe organics dried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe solid was triturated with ethyl acetate
  5. filtrationfiltered
  6. customthe filtrate purified by chromatography on silica eluting with 3% ethyl acetate in toluene

Sources & evidence

ORD record
ord-8f40eacb5a7e497b877b45bf4af7c22d
Source dataset
uspto-grants-2006_10
Patent number
US07125881B2

Reaction notes

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