Hydrochloric Acid → Ethyl 2-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)acetate

HRID 2067883Notes

Reaction equation

HRID 2067883 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.Cl[C:15]1[N:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH:28]([F:30])[F:29])=[CH:23][CH:22]=2)=[CH:17][N:16]=1.CC1C=CC(S(O)(=O)=O)=CC=1.Cl>O1CCOCC1>[F:30][CH:28]([F:29])[O:27][C:24]1[CH:23]=[CH:22][C:21]([C:18]2[CH:19]=[N:20][C:15]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=3)=[N:16][CH:17]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 225219p-Aminophenylacetic acid ethyl esterHCID 581719302-Chloro-5-(4-(difluoromethoxy)phenyl)pyrimidine

Product 1

HCID 68727105Ethyl 2-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 2-(4-aminophenyl)acetate (8 mmol), 2-chloro-5-(4-(difluoromethoxy)phenyl)pyrimidine 30 (4 mmol), and p-TSA (2 mmol) in 1,4-dioxane (4 mL) are heated at reflux for 4 h. The mixture is poured onto 1 N HCl. The solid is filtered, washed with 1 N HCl and dried to afford ethyl 2-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)acetate 31 as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 2H), 7.92 (s, 1H), 7.54 (d, J=8.5 Hz, 2H), 7.43 (d, J=8.6 Hz, 2H), 7.23 (d, J=8.6 Hz, 2H), 7.18 (d, J=9.1 Hz, 2H), 6.49 (t, J=73.5 Hz, 1H), 4.09 (q, J=7.1 Hz, 2H), 3.54 (s, 2H), 1.19 (t, J=7.1 Hz, 3H). MS (m/z) (M+1)+: 400.1.

Workup

  1. temperatureare heated
  2. temperatureat reflux for 4 h
  3. filtrationThe solid is filtered
  4. washwashed with 1 N HCl
  5. customdried

Sources & evidence

ORD record
ord-f8cde02fa238461d9e9b62a5cea959b9
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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