Hydrochloric Acid → HCID 86640256, compound

HRID 422105Notes

Reaction equation

HRID 422105 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]3[C:13]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][C:18]=4[O:23]COC)=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=2)[C:5]([F:27])=[CH:4][N:3]=1.Cl>C1COCC1.C(=O)(O)[O-].[Na+].ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]3[C:13]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][C:18]=4[OH:23])=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=2)[C:5]([F:27])=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86640257HCID 86640257, compound

Product 1

HCID 86640256HCID 86640256, compoundYield 8.4%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Treat a solution of 2-chloro-5-fluoro-4-[7-(3-methoxymethoxy-pyridin-4-yl)-benzo[b]thiophen-2-yl]-pyrimidine (4 g, 10 mmol) in THF (10 mL) with 5 N HCl (3 mL). Stir the mixture at room temperature for 6 hours. Concentrate the reaction in vacuo and dilute with saturated aqueous sodium bicarbonate and dichloromethane. Separate the layers and filter each layer. Wash the solid from the organic phase with dichloromethane to give the title compound (300 mg) as a tan solid. Wash the solid from the aqueous layer with water and dry to give the title compound (300 mg) as a tan solid. Combine the solids to give the title compound (600 mg, 17%) as a tan solid. MS (ES) m/z 358 [M+1]+.

Workup

  1. concentrationConcentrate
  2. customthe reaction in vacuo
  3. customSeparate the layers
  4. filtrationfilter each layer
  5. washWash the solid from the organic phase with dichloromethane

Sources & evidence

ORD record
ord-183583f0547448d8a99704a5c929d2ca
Source dataset
uspto-grants-2012_01
Patent number
US08101628B2

Reaction notes

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