Hydrochloric Acid → HCID 178424775, compound

HRID 80767Notes

Reaction equation

HRID 80767 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:10]=[C:11]([O:28]C)[C:12]2[CH2:18][N:17]([C:19]3[N:23]([CH3:24])[N:22]=[C:21]([CH:25]([CH3:27])[CH3:26])[CH:20]=3)[CH2:16][CH2:15][C:13]=2[N:14]=1.Cl.O.C([O-])(O)=O.[Na+]>CCO>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[N:10]=[C:11]([OH:28])[C:12]2[CH2:18][N:17]([C:19]3[N:23]([CH3:24])[N:22]=[C:21]([CH:25]([CH3:26])[CH3:27])[CH:20]=3)[CH2:16][CH2:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 712446912-(2,6-dimethylphenyl)-6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Product 1

HCID 178424775HCID 178424775, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(2,6-dimethylphenyl)-6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (3.3 g, 8.51 mmol) in EtOH (30 mL) in a 150 mL sealed tube was added concentrated hydrochloride (21 mL). The tube was sealed, stirred, and heated at 90° C. for 16 h. The reaction mixture was cooled to r.t. and poured onto iced-water. Solid NaHCO3 was added to neutralize the mixture. The mixture was extracted by DCM three times. The combined organic layers were dried over Na2SO4. After filtration and concentration, the resulting residue was purified via silica gel FCC (0-100% EtOAc/heptane) to give 2-(2,6-dimethylphenyl)-6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ol. 1H NMR (400 MHz, CD2Cl2) δ ppm 9.95 (br. s., 1 H), 7.21-7.36 (m, 1 H), 7.13 (d, J=7.3 Hz, 2 H), 5.76 (s, 1 H), 3.87 (s, 2 H), 3.68 (s, 3 H), 3.22 (t, J=5.7 Hz, 2 H), 2.77-2.97 (m, 3 H), 2.22 (s, 6 H), 1.22 (d, J=7.1 Hz, 6 H). MS (ESI+) m/z 378.3 (M+H)+.

Workup

  1. customThe tube was sealed
  2. temperatureThe reaction mixture was cooled to r.t.
  3. extractionThe mixture was extracted by DCM three times
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe resulting residue was purified via silica gel FCC (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-cd58825a433e406b9039c05b164c67dd
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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