Hydrochloric Acid → HCID 178517540, compound

HRID 1507504Notes

Reaction equation

HRID 1507504 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([Cl:30])=[N:12][C:13]([CH:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[N:14][C:15]=1[OH:16].Cl>CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:15]([OH:16])=[N:14][C:13]([CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)=[N:12][C:11]=1[Cl:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178451808HCID 178451808, compound

Product 1

HCID 178517540HCID 178517540, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution of tert-butyl 4-[5-(1,3-benzothiazol-2-yl)-4-chloro-6-hydroxypyrimidin-2-yl]piperidine-1-carboxylate (44.7 g, 100.01 mmol, 1.00 equiv) in methanol (50 ml) was added concentrated hydrochloric acid (50 mL, 12 M). The resulting solution was stirred for 30 min at room temperature. Concentration under vacuum gave 34 g of 5-(1,3-benzothiazol-2-yl)-6-chloro-2-(piperidin-4-yl)pyrimidin-4-ol as a yellow solid, which was used directly for next step without further purification. MS m/z [M+H](ESI): 347.

Workup

  1. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-bd1135f847474bb9bc2305e9ca91e855
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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