HCID 66616333, compound → HCID 16062389, compound

HRID 1917277Notes

Reaction equation

HRID 1917277 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH2:20][N:19](C(=O)C)[CH2:18][CH2:17][C:10]=3[N:11]=[C:12]([CH:14]([CH3:16])[CH3:15])[N:13]=2)=[CH:4][CH:3]=1>Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH2:20][NH:19][CH2:18][CH2:17][C:10]=3[N:11]=[C:12]([CH:14]([CH3:16])[CH3:15])[N:13]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 66616333HCID 66616333, compound

Product 1

HCID 16062389HCID 16062389, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of crude 1-[4-(4-fluoro-phenyl)-2-isopropyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-ethanone in 10% aq. HCl (800 mL) was heated at reflux for 2 h and then cooled to rt. The aqueous solution was washed with EtOAc (400 mL) and then was basified with NaOH pellets (˜120 g) to pH>12. The basic solution was extracted with CH2Cl2 (2×500 mL). The combined organic layers were washed with 1 N NaOH (400 mL), dried (MgSO4), and concentrated to give the crude product (100 g), which was used in the next reaction without further purification. HPLC: RT=6.89 min. MS (ESI): exact mass calcd. for C16H18FN3, 271.15; m/z found, 271.9 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. washThe aqueous solution was washed with EtOAc (400 mL)
  4. extractionThe basic solution was extracted with CH2Cl2 (2×500 mL)
  5. washThe combined organic layers were washed with 1 N NaOH (400 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4ac668b6872647628bdd567c9dca40ec
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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