1,1'-Carbonyldiimidazole → HCID 118023243, compound

HRID 2171816Notes

Reaction equation

HRID 2171816 reaction equation
[CH:1]1([C:7]2[S:23][C:10]3[N:11]=[C:12]([CH3:22])[N:13]=[C:14]([CH2:15][NH:16][C:17]([CH3:21])([CH3:20])[CH2:18][OH:19])[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1N=CN([C:29](N2C=NC=C2)=[O:30])C=1>C(Cl)Cl>[CH:1]1([C:7]2[S:23][C:10]3[N:11]=[C:12]([CH3:22])[N:13]=[C:14]([CH2:15][N:16]4[C:17]([CH3:20])([CH3:21])[CH2:18][O:19][C:29]4=[O:30])[C:9]=3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 118024026HCID 118024026, compound

Product 1

HCID 118023243HCID 118023243, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-{[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]amino}-2-methylpropan-1-ol (55 mg) and DCM was added CDI (40 mg), followed by stirring at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column (hexane/EtOAc) to obtain 3-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]-4,4-dimethyl-1,3-oxazolidin-2-one (54 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-b1b1f9072b974a7d838cb20809648a5c
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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