Acetyl chloride → HCID 66857789, compound

HRID 253029Notes

Reaction equation

HRID 253029 reaction equation
[C:1]([Si:5]([CH3:38])([CH3:37])[O:6][C:7]1[CH:8]=[C:9]([C:13]2[N:14]=[C:15]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[C:16]3[S:21][C:20]([CH2:22][N:23]4[CH2:28][C@H:27]([CH3:29])[NH:26][C@H:25]([CH3:30])[CH2:24]4)=[CH:19][C:17]=3[N:18]=2)[CH:10]=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:46](Cl)(=[O:48])[CH3:47]>ClCCl>[C:1]([Si:5]([CH3:38])([CH3:37])[O:6][C:7]1[CH:8]=[C:9]([C:13]2[N:14]=[C:15]([N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)[C:16]3[S:21][C:20]([CH2:22][N:23]4[CH2:24][C@H:25]([CH3:30])[N:26]([C:46](=[O:48])[CH3:47])[C@H:27]([CH3:29])[CH2:28]4)=[CH:19][C:17]=3[N:18]=2)[CH:10]=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66857824HCID 66857824, compound

Product 1

HCID 66857789HCID 66857789, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-6-((3R,5S)-3,5-dimethyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (80 mg, 0.14 mmol) in dichloromethane (5 mL) was added triethylamine (40 μL, 2.0 equivalents) followed by acetyl chloride (15 μL, 1.5 eq.). After stirring overnight, the reaction mixture was diluted with dichloromethane, washed with aqueous sodium carbonate solution, dried (MgSO4) and the solvent removed in vacuo to yield 1-((2R,6S)-4-{2-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl}-2,6-dimethyl-piperazin-1-yl)-ethanone (80 mg) as a white solid. Removal of the tert-butyldimethylsilyl protecting group was performed as described above to yield the title compound.

Workup

  1. washwashed with aqueous sodium carbonate solution
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3d7cfe7766e84f399c82d99e452bc7b6
Source dataset
uspto-grants-2011_01
Patent number
US07872003B2

Reaction notes

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