Triethylamine → N2-[4-(dimethylphosphoryl)phenyl]-N'-(morpholin-4-ylmethyl)-5(trifluoromethyl)pyrimidine-2,4-diamine

HRID 1471946Notes

Reaction equation

HRID 1471946 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([P:19]([CH3:22])([CH3:21])=[O:20])=[CH:15][CH:14]=2)[N:3]=1.C([N:25](CC)CC)C.NC[CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>C(O)C>[CH3:21][P:19]([C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:4]2[N:3]=[C:2]([NH:25][CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[CH:14][CH:15]=1)([CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4082852-MorpholinoethylamineHCID 866687884-chloro-N-[4-(dimethylphosphoryl)phenyl]-5-(trifluoromethyl)pyrimidin-2-amine

Product 1

HCID 68165213N2-[4-(dimethylphosphoryl)phenyl]-N'-(morpholin-4-ylmethyl)-5(trifluoromethyl)pyrimidine-2,4-diamineYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-N-[4-(dimethylphosphoryl)phenyl]-5-(trifluoromethyl)pyrimidin-2-amine (prepared as in Example 1: 40 mg, 0.12 mmol) in 2 mL of ethanol was added 50 μL of triethylamine and 4-(2-aminoethyl) morpholine (15 mg, 0.12 mmol). The mixture was microwave at 120 degrees for 20 minutes. The reaction mixture was filtered through a syringe filter and purified by prep-HPLC (Waters Sunfire C18 column with ACN/water mobile phases) to yield a white solid as product (42 mg, 81% yield.) MS/ES+: m/z=430.

Workup

  1. customat 120 degrees
  2. customfor 20 minutes
  3. filtrationThe reaction mixture was filtered through a syringe
  4. filtrationfilter
  5. custompurified by prep-HPLC (Waters Sunfire C18 column with ACN/water mobile phases)
  6. customto yield a white solid as product (42 mg, 81% yield.) MS/ES+

Sources & evidence

ORD record
ord-203df6f749584720a3c2e4bacd6c4bac
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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