Diisopropylethylamine → 1-[2-(4-Benzo[b]thiophen-2-yl-5-bromo-pyrimidin-2-ylamino)-ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione

HRID 2267295Notes

Reaction equation

HRID 2267295 reaction equation
[S:1]1[C:5]([C:6]2[C:11]([Br:12])=[CH:10][N:9]=[C:8](Cl)[N:7]=2)=[CH:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2.[NH2:18][CH2:19][CH2:20][N:21]1[C:25]2([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:24](=[O:31])[NH:23][C:22]1=[O:32].C(N(C(C)C)CC)(C)C>C(O)(C)C>[S:1]1[C:5]([C:6]2[C:11]([Br:12])=[CH:10][N:9]=[C:8]([NH:18][CH2:19][CH2:20][N:21]3[C:25]4([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[C:24](=[O:31])[NH:23][C:22]3=[O:32])[N:7]=2)=[CH:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 574288061-(2-Aminoethyl)-1,3-diaza-spiro[4.5]decane-2,4-dioneHCID 574288214-(Benzo[b]thiophen-2-yl)-5-bromo-2-chloropyrimidine

Product 1

HCID 602042471-[2-(4-Benzo[b]thiophen-2-yl-5-bromo-pyrimidin-2-ylamino)-ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 4-benzo[b]thiophen-2-yl-5-bromo-2-chloro-pyrimidine (318 mg, 1.0 mmol) and 1-(2-aminoethyl)-1,3-diaza-spiro[4.5]decane-2,4-dione (214 mg, 1.01 equiv.) in isopropyl alcohol (4 mL) was treated with diisopropylethylamine (192 μL, 1.1 equiv.) and heated at 170° C. for 17 min in a Personal Chemistry microwave reactor. Upon cooling, the product was obtained by filtration and washing with isopropyl alcohol, recrystallizing from hot isopropyl alcohol. MS (M+H)+ 500/502.

Workup

  1. temperatureUpon cooling
  2. customthe product was obtained by filtration
  3. washwashing with isopropyl alcohol
  4. customrecrystallizing from hot isopropyl alcohol

Sources & evidence

ORD record
ord-d81539a4ab084b1580c3662924945db3
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

Loading…