Carbon tetrabromide → HCID 89579534, compound

HRID 928610Notes

Reaction equation

HRID 928610 reaction equation
Br[C:2]([Br:5])(Br)Br.OC[CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:28][S:27][C:16]=3[N:17]=[C:18]([CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][C:22]3=[O:26])[N:19]=2)[CH2:10][CH2:9]1>ClCCl>[Br:5][CH2:2][CH:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]3[C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:28][S:27][C:16]=3[N:17]=[C:18]([CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][C:22]3=[O:26])[N:19]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 11205Carbon tetrabromideHCID 89579872HCID 89579872, compound

Product 1

HCID 89579534HCID 89579534, compoundYield 136.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tetrabromomethane (120 mg) was added to a solution of 1-[[4-[4-(hydroxymethyl)-1-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]methyl]pyrrolidin-2-one (102 mg) in dichloromethane (10 mL). Polystyrene-supported triphenylphosphine (0.35 g, 2.04 mmol g-1) was added and the mixture was stirred overnight at room temperature. The solid material was filtered off and the solvent was evaporated to give the target compound as a yellow solid (160 mg). m/z [M+H]+ 484.9/486.9. Retention time 4.97 min (LCMS method+ve 6 min).

Workup

  1. filtrationThe solid material was filtered off
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-02c69d69293c416bb01dcea075357b0f
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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