Hydrochloric Acid → HCID 86690742, compound

HRID 1471691Notes

Reaction equation

HRID 1471691 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([C:16]2[N:20]([CH3:21])[N:19]=[CH:18][CH:17]=2)=[N:12][CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.[Si](OC[C:31]1[C:32]([C:37]2[CH:41]=[CH:40][N:39]([CH3:42])[N:38]=2)=[N:33][CH:34]=[CH:35][CH:36]=1)(C(C)(C)C)(C)C.Cl>CO>[CH3:21][N:20]1[C:16]([C:11]2[C:10]([CH2:9][OH:8])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:17][CH:18]=[N:19]1.[CH3:42][N:39]1[CH:40]=[CH:41][C:37]([C:32]2[CH:31]=[CH:36][C:35]([CH2:9][OH:8])=[CH:34][N:33]=2)=[N:38]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 86690744HCID 86690744, compoundHCID 86690745HCID 86690745, compound

Product 2

HCID 86690742HCID 86690742, compoundYield 72%HCID 86690743HCID 86690743, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-((tert-butyldimethylsilyloxy)methyl)-2-(1-methyl-1H-pyrazol-5-yl)pyridine and 3-((tert-butyldimethylsilyloxy)methyl)-2-(1-methyl-1H-pyrazol-3-yl)pyridine (420 mg, 1.38 mmol) in MeOH (20 mL) was added HCl (4 N, 2.0 mL). The mixture was stirred at rt for 1 h, concentrated, and diluted with EtOAc (50 mL) and NaHCO3(sat) solution (10 mL). The layers were separated and aqueous layer was extracted with EtOAc three times. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using EtOAc as eluent to give (2-(1-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methanol (187 mg, 72%) and (2-(1-methyl-1H-pyrazol-3-yl)pyridin-5-yl)methanol (55 mg, 21%) as white solids. Data for 2-(1-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methanol: 1H NMR (400 MHz; CDCl3) 8.58 (d, 1H), 7.91 (d, 1H), 7.46 (s, 1H), 7.30 (dd, 1H), 6.36 (s, 1H), 4.62 (d, 2H), 3.83 (s, 3H), 2.1 (t, 1H). LRMS (M+H+) m/z 190.1; data for (2-(1-methyl-1H-pyrazol-3-yl)pyridin-5-yl)methanol: 1H NMR (400 MHz; CDCl3) 8.60 (d, 1H), 7.70 (d, 1H), 7.47 (s, 1H), 7.22 (dd, 1H), 6.99 (s, 1H), 5.91 (t, 1H), 4.68 (d, 2H), 4.01 (s, 3H). LRMS (M+H+) m/z 190.1

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc (50 mL) and NaHCO3(sat) solution (10 mL)
  3. customThe layers were separated
  4. extractionaqueous layer was extracted with EtOAc three times
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified on silica gel

Sources & evidence

ORD record
ord-642b76dbe4c14dcdae3272785558e35e
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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