1,2-Dimethoxyethane → HCID 68867790, compound

HRID 2374937Notes

Reaction equation

HRID 2374937 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[NH:13][C:12](=O)[C:11]2=[C:15](C)[N:16]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[N:10]2[N:9]=1.[CH3:29]OCCOC>>[CH3:29][C:8]1([NH2:7])[NH:13][CH2:12][C:11]2=[CH:15][N:16]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[N:10]2[NH:9]1

Participants

4

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 21226445Aluminium lithium hydrideHCID 135984673HCID 135984673, compound2×

Product 1

HCID 68867790HCID 68867790, compound

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride was added in portions to a stirring solution of 2-amino-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-4(3H)-one (Intermediate 43) (2.0 g, 6.47 mmol) in DME (50 mL) at rt. The resultant mixture was then heated to reflux for 2 h. The reaction mixture was then cooled to 0° C. and carefully quenched with H2O. After extraction into EtOAc., the combined organic extracts were dried (MgSO4), filtered, and concentrated. Purification of the residue by chromatography afforded 2-methyl-7-[3-(trifluoromethyl)phenyl]-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-amine (0.60 g) as a pale yellow solid. 1H NMR (DMSO-d6): δ8.67-8.60 (m, 1H), 8.54 (s, 1H), 7.61-7.54 (m, 2H), 6.55 (s, 1H), 5.50 (s, 2H), 4.35 (s, 2H), 2.06 (s, 3H). MS m/z 294 (M−1).

Workup

  1. temperatureto reflux for 2 h
  2. customcarefully quenched with H2O
  3. extractionAfter extraction into EtOAc
  4. dry with material, the combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by chromatography

Sources & evidence

ORD record
ord-a0cd4995c02a41beae1595535e12f54a
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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