Ethyl isocyanate → 1-[5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-3-ethyl-urea

HRID 81784Notes

Reaction equation

HRID 81784 reaction equation
[NH2:1][C:2]1[C:3]([O:20][CH3:21])=[CH:4][C:5]([CH:17]([CH3:19])[CH3:18])=[C:6]([CH:16]=1)[O:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.[CH2:22]([N:24]=[C:25]=[O:26])[CH3:23]>C1(C)C=CC=CC=1>[NH2:14][C:11]1[N:10]=[C:9]([NH2:15])[C:8]([O:7][C:6]2[C:5]([CH:17]([CH3:19])[CH3:18])=[CH:4][C:3]([O:20][CH3:21])=[C:2]([NH:1][C:25]([NH:24][CH2:22][CH3:23])=[O:26])[CH:16]=2)=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 595985735-(5-Amino-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

Product 1

HCID 573297051-[5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-3-ethyl-ureaYield 83.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-(5-amino-2-Isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (0.117 g, 0.4 mmol) and ethyl isocyanate (0.034 g, 0.5 mmol) in 4 mL of toluene was heated to 100° C. in a sealed tube. After 5 h the solution was cooled and concentrated in vacuo gave a brown solid. Purification via flash chromatography (CH2Cl2/MeOH 97:3) afforded 1-[5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-3-ethyl-urea (0.120 g, 83%) as a white solid; (M+H)=361.

Workup

  1. temperatureAfter 5 h the solution was cooled
  2. concentrationconcentrated in vacuo
  3. customgave a brown solid
  4. customPurification via flash chromatography (CH2Cl2/MeOH 97:3)

Sources & evidence

ORD record
ord-8e9e2eb50c1d4939b099a3fac40a877f
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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