Diisopropyl Ether → 1-(2-Chloro-ethyl)-3-[3-(8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydro-pteridin-2-ylamino)-5-methylsulfonyl-phenyl]urea

HRID 1957997Notes

Reaction equation

HRID 1957997 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]2[N:22]=[CH:21][C:20]3[N:19]([CH3:23])[C:18](=[O:24])[CH2:17][N:16]([CH:25]([CH3:27])[CH3:26])[C:15]=3[N:14]=2)[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.[Cl:28][CH2:29][CH2:30][N:31]=[C:32]=[O:33].C(OC(C)C)(C)C>O1CCOCC1>[Cl:28][CH2:29][CH2:30][NH:31][C:32]([NH:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[C:4]([NH:12][C:13]2[N:22]=[CH:21][C:20]3[N:19]([CH3:23])[C:18](=[O:24])[CH2:17][N:16]([CH:25]([CH3:27])[CH3:26])[C:15]=3[N:14]=2)[CH:3]=1)=[O:33]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 160352-Chloroethyl isocyanateHCID 592861742-(3-Amino-5-(methylsulfonyl)-phenylamino)-8-isopropyl-5-methyl-7,8-dihydro-5H-pteridin-6-one

Product 1

HCID 592861421-(2-Chloro-ethyl)-3-[3-(8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydro-pteridin-2-ylamino)-5-methylsulfonyl-phenyl]urea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

2-(3-Amino-5-(methylsulfonyl)-phenylamino)-8-isopropyl-5-methyl-7,8-dihydro-5H-pteridin-6-one (300 mg; 0.768 mmol) was diluted under nitrogen atmosphere in 3 ml of dry 1,4-dioxane, then a solution of 2-chloroethyl-isocyanate (0.09 ml; 0.999 mmol) in 2 ml of dry 1,4-dioxane was added drop-wise. The reaction mixture was stirred at room temperature for 3 h, then warmed to 60° C. and maintained at that temperature for 3 h. The reaction mixture was then concentrated in vacuo. The crude obtained was treated with isopropyl ether. The solid obtained was filtered. 261 mg (0.001 mol; 68.5 yield) of the desired compound were obtained.

Workup

  1. temperaturewarmed to 60° C.
  2. temperaturemaintained at that temperature for 3 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customThe crude obtained
  5. customThe solid obtained
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-013e7cd7197c42dcad81822a7d78c115
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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