Hydrochloric Acid → HCID 178477981, compound

HRID 42301Notes

Reaction equation

HRID 42301 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[N:17](C4CCCCO4)[N:16]=[CH:15][CH:14]=3)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:24].CC(OC)(C)C>CO>[ClH:24].[C:1]1([C:7]2[N:8]=[CH:9][C:10]([C:13]3[CH:14]=[CH:15][NH:16][N:17]=3)=[CH:11][N:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 59252422HCID 59252422, compound

Product 1

HCID 178477981HCID 178477981, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Phenyl-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyrimidine (Step A, 51 mg) was added to a 1 N hydrochloric acid solution in methanol (5 mL). The solution was stirred at room temperature for two hours. MTBE (40 mL) was added to precipitate a white solid which was filtered and rinsed with MTBE and dried under high vacuum. The title compound was obtained as a white powder (11.4 mg, 27% yield); melting point 264-273° C.; 1H-NMR (300 MHz; CD3OD) δ 10.0 (s, 1H), 9.29 (s, 2H), 8.44 (dd, 2H), 7.86 (d, 1H), 7.54 (m, 3H), 6.95 (d, 1H); MS (ESI+) m/z 223 (M+1); H-PGDS FPBA IC50: 2.4 μM.

Workup

  1. customto precipitate a white solid which
  2. filtrationwas filtered
  3. washrinsed with MTBE
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-60e485fc08234504b2eeb28c84423004
Source dataset
uspto-grants-2013_09
Patent number
US08536185B2

Reaction notes

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