Hydrochloric Acid → HCID 86640256, compound

HRID 1640920Notes

Reaction equation

HRID 1640920 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+].C(Cl)Cl>[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 RT for 6 h. Concentrate the reaction in vacuo and dilute with saturated aqueous sodium bicarbonate and DCM. Separate the phases and filter each phase. Wash the solid from the organic phase with DCM 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 phases
  4. filtrationfilter each phase
  5. washWash the solid from the organic phase with DCM

Sources & evidence

ORD record
ord-00853f3fd67b4b14b05bd32a23bc0ef7
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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