Methanol, 1,1-diethoxy-, 1-acetate → 7-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-8-propyl-[1,2,4]triazolo[4,3-c]-pyrimidine

HRID 916672Notes

Reaction equation

HRID 916672 reaction equation
[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]=[C:16]([NH:20][NH2:21])[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:25](OC(OCC)OCC)(=O)C.C([O-])(O)=O.[Na+]>ClCCl>[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]4[CH:25]=[N:21][N:20]=[C:16]4[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 516892Sodium BicarbonateHCID 57503304{6-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-hydrazine

Product 1

HCID 575032587-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-8-propyl-[1,2,4]triazolo[4,3-c]-pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 131 (30 mg, 0.09 mmol) and diethoxymethyl acetate (1 mL) is stirred at room temperature for 10 minutes. NaHCO3 (aq.) (10 mL) and dichloromethane (10 mL) are added. The organic layer is separated and the aqueous layer is extracted with dichloromethane (2×10 mL). The combined organic layers are dried (NaSO4) and solvent removed. The crude product is separated by PTLC (10% methanol in dichloromethane) to yield 187; LC-MS, M+1 338.15; 1H-NMR (CDCl3) δ: 8.87 (s, 1H), 8.83 (s, 1H), 8.42 (s, 1H), 7.54 (t, 1H), 7.23–7.34 (m, 3H), 5.79 (s, 2H), 3.02 (t, 2H), 1.66–1.76 (m, 2H), 0.99 (t, 3H).

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with dichloromethane (2×10 mL)
  3. dry with materialThe combined organic layers are dried (NaSO4) and solvent
  4. customremoved
  5. customThe crude product is separated by PTLC (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9c3c24628f194f7a941cba8b4e961e83
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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