Butyl glycidyl ether → HCID 59151333, compound

HRID 888955Notes

Reaction equation

HRID 888955 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[C:13]4[S:18][C:17]([CH2:19][N:20]5[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:32]([O:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:33]1[O:35][CH2:34]1>CN(C)C=O>[CH2:37]([O:36][CH2:32][CH:33]([OH:35])[CH2:34][N:23]1[CH2:22][CH2:21][N:20]([CH2:19][C:17]2[S:18][C:13]3[C:12]([N:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)=[N:11][C:10]([C:5]4[CH:6]=[CH:7][CH:8]=[C:9]5[C:4]=4[CH:3]=[CH:2][NH:1]5)=[N:15][C:14]=3[CH:16]=2)[CH2:25][CH2:24]1)[CH2:38][CH2:39][CH3:40]

Participants

4

Reactant 2

HCID 17049Butyl glycidyl ether2×HCID 11517696HCID 11517696, compound

Product 1

HCID 59151333HCID 59151333, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(1H-indol-4-yl)-4-morpholin-4-yl-6-piperazin-1-ylmethyl-thieno[3,2-d]pyrimidine (50 mg) in N,N-dimethylformamide (3 mL) at r.t. was added 0.1 M Na2HPO4pH 6.8 buffer (0.5 mL) and butyl glycidyl ether (18 μL) and the resulting cloudy mixture was heated at 55° C. for 3 days with 2 extra equivalents of butyl glycidyl ether (18 μL) added during this time. The reaction mixture was partitioned between EtOAc (15 mL) and brine (15 mL), the organic layer was dried (Na2SO4), concentrated and the residue purified by flash chromatography (silica; 96:4 EtOAc/MeOH as eluent) to give an off-white solid (38 mg).

Workup

  1. additionadded during this time
  2. customThe reaction mixture was partitioned between EtOAc (15 mL) and brine (15 mL)
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography (silica; 96:4 EtOAc/MeOH as eluent)

Sources & evidence

ORD record
ord-9bac82cec88a488f90271ea183a73140
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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