Diisopropylethylamine → (S)-tert-Butyl 2-(4-(2,5-dichloropyrimidin-4-ylamino)phenyl)morpholine-4-carboxylate

HRID 710272Notes

Reaction equation

HRID 710272 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[Cl:21][C:22]1[N:27]=[C:26](Cl)[C:25]([Cl:29])=[CH:24][N:23]=1.C(N(C(C)C)CC)(C)C>CC(O)C>[Cl:21][C:22]1[N:27]=[C:26]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]3[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]3)=[CH:4][CH:3]=2)[C:25]([Cl:29])=[CH:24][N:23]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 66705988(S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate

Product 1

HCID 86671412(S)-tert-Butyl 2-(4-(2,5-dichloropyrimidin-4-ylamino)phenyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (S)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (100 mg, 0.36 mmol), 2,4,5-trichloropyrimidine (66 mg, 0.36 mmol) and diisopropylethylamine (70 mg, 0.54 mmol) was dissolved in 2-propanol (1.5 ml) and shaken at 80° C. overnight. Most of the solvent was evaporated. Ammonium chloride solution was added and the mixture was extracted with ethyl acetate twice. The combined organic layers are dried (MgSO4) and evaporated.

Workup

  1. customMost of the solvent was evaporated
  2. additionAmmonium chloride solution was added
  3. extractionthe mixture was extracted with ethyl acetate twice
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-1a73a0e76d3e4552ad461879e4cba360
Source dataset
uspto-grants-2015_11
Patent number
US09181230B2

Reaction notes

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