Trimethylsilyl iodide → HCID 178424664, compound

HRID 1970950Notes

Reaction equation

HRID 1970950 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=2)[N:12]=[C:11]([C:22]2[CH:23]=[C:24]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([N:36]4[CH2:41][CH2:40][N:39]([CH:42]([CH3:44])[CH3:43])[CH2:38][CH2:37]4)=[O:35])=[CH:30][CH:29]=3)[CH:25]=[N:26][CH:27]=2)[CH:10]=1)C1C=CC=CC=1.C[Si](I)(C)C>C(Cl)Cl>[OH:8][C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=2)[N:12]=[C:11]([C:22]2[CH:23]=[C:24]([C:28]3[CH:29]=[CH:30][C:31]([C:34]([N:36]4[CH2:37][CH2:38][N:39]([CH:42]([CH3:44])[CH3:43])[CH2:40][CH2:41]4)=[O:35])=[CH:32][CH:33]=3)[CH:25]=[N:26][CH:27]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 44197797HCID 44197797, compound

Product 1

HCID 178424664HCID 178424664, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (4-{5-[6-benzyloxy-2-(6-methyl-pyridin-2-yl)-pyrimidin-4-yl]-pyridin-3-yl}-phenyl)-(4-isopropyl-piperazin-1-yl)-methanone (Example 8) (1 eq, 30 mg) in dry DCM (0.6 ml) under an atmosphere of N2 is treated with trimethylsilyl iodide (12 eq, 83.6 μl). After stirring at RT overnight, the reaction is quenched by addition of MeOH (5 ml) and stirring continued for 45 minutes. The solvent is removed in vacuo and the residue is loaded onto a SCX-2 cartridge (1 g) eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are combined and concentrated in vacuo and dried under vacuum overnight to afford the title compound [M+H]+=495 as a white solid.

Workup

  1. customthe reaction is quenched by addition of MeOH (5 ml)
  2. stirringstirring
  3. waitcontinued for 45 minutes
  4. customThe solvent is removed in vacuo
  5. washeluting with MeOH
  6. concentrationconcentrated in vacuo
  7. customdried under vacuum overnight

Sources & evidence

ORD record
ord-309abb9c73fe40bb9f8b18fe318c2a53
Source dataset
uspto-grants-2013_04
Patent number
US08431578B2

Reaction notes

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