Trifluoroacetic acid → 7-(4-(Piperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidin-5-ol

HRID 1853036Notes

Reaction equation

HRID 1853036 reaction equation
[OH:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[N:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH:20]1[CH2:19][CH2:18][CH:17]([C:14]2[CH:13]=[CH:12][C:11]([C:4]3[N:3]=[C:2]([OH:1])[N:7]4[CH:8]=[CH:9][N:10]=[C:6]4[CH:5]=3)=[CH:16][CH:15]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451737HCID 178451737, compound

Product 1

HCID 1785174297-(4-(Piperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidin-5-olYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask charged with tert-butyl 4-(4-(5-hydroxyimidazo[1,2-c]pyrimidin-7-yl)phenyl)piperidine-1-carboxylate (1.75 g, 4.44 mmol) in 40 mL of dichloromethane was added 2,2,2-trifluoroacetic acid (15 mL, 195 mmol) at ambient temperature for 3 hours. The solvent was concentrated under reduced pressure and the resulting crude was taken up in methanol (10 mL) and to it was added aqueous saturated sodium bicarbonate slowly. The resulting solid was collected by means of vacuum filtration and was dried overnight on high vacuum. This solid was triturated with water (50 mL) and solids were collected by means of vacuum filtration and dried on high vacuum to afford 7-(4-(piperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidin-5-ol (1.03 g, 3.50 mmol, 78.9% yield). MS (apci) m/z=295.1 (M+H).

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. additionwas added aqueous saturated sodium bicarbonate slowly
  3. filtrationThe resulting solid was collected by means of vacuum filtration
  4. customwas dried overnight on high vacuum
  5. customThis solid was triturated with water (50 mL) and solids
  6. filtrationwere collected by means of vacuum filtration
  7. customdried on high vacuum

Sources & evidence

ORD record
ord-061046b9e48d4579a2f8a9fde65112a7
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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