3-Methoxy-1-propanol → 3-Ethyl-5-[5-(4-ethylpiperazin-1-ylsulphonyl)-2-(3-methoxyprop-1-oxy)-pyridin-3-yl]-2-(pyridin-2-yl)methyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-one

HRID 990226Notes

Reaction equation

HRID 990226 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]2[NH:11][C:12](=[O:28])[C:13]3[C:14](=[C:16]([CH2:26][CH3:27])[N:17]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[N:18]=3)[N:15]=2)=[CH:8][C:7]([S:29]([N:32]2[CH2:37][CH2:36][N:35]([CH2:38][CH3:39])[CH2:34][CH2:33]2)(=[O:31])=[O:30])=[CH:6][N:5]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:50][O:51][CH2:52]CCO>>[CH2:26]([C:16]1[N:17]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[N:18]=[C:13]2[C:12](=[O:28])[NH:11][C:10]([C:9]3[C:4]([O:3][CH2:1][CH2:2][CH2:50][O:51][CH3:52])=[N:5][CH:6]=[C:7]([S:29]([N:32]4[CH2:37][CH2:36][N:35]([CH2:38][CH3:39])[CH2:34][CH2:33]4)(=[O:30])=[O:31])[CH:8]=3)=[N:15][C:14]=12)[CH3:27]

Participants

4

Reactant 3

HCID 741163-Methoxy-1-propanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 1355816594-{6-Ethoxy-5-[3-ethyl-6,7-dihydro-7-oxo-2-(2-pyridylmethyl)-2H-pyrazolo [4,3-d]pyrimidin-5-yl]-3-pyridylsulfonyl}-1-ethylpiperazine

Product 1

HCID 1364368763-Ethyl-5-[5-(4-ethylpiperazin-1-ylsulphonyl)-2-(3-methoxyprop-1-oxy)-pyridin-3-yl]-2-(pyridin-2-yl)methyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-oneYield 38%

Conditions

Temperature
90 °C

Procedure

A mixture of the title compound of Example 1 (200 mg, 0.36 mmol), potassium bis(trimethylsilyl)amide (361 mg, 1.81 mmol) and 3-methoxypropan-1-ol (1.5 ml) was stirred at 90° C. for 18 hours, then allowed to cool. The resulting mixture was evaporated under reduced pressure and the residue purified by column chromatography on silica gel, using an elution gradient of dichloromethane:methanol (97:3 to 95:5), to give the title compound (81 mg, 38%) as a foam. Found: C, 55.36; H, 6.11; N, 18.18. C28H36N8O5S; 0.50 H2O requires C, 55.52; H, 6.16; N, 18.50%. δ (CDCl3): 1.01 (3H, t), 1.29 (3H, t), 2.19 (2H, m), 2.40 (2H, q), 2.54 (4H, m), 3.02 (2H, q), 3.12 (4H, m), 3.39 (3H, s), 3.65 (2H, t), 4.76 (2H, t), 5.68 (2H, s), 7.09 (1H, d), 7.21 (1H, m), 7.62 (1H, m), 8.56 (1H, d), 8.62 (1H, s), 8.93 (1H, s), 10.84 (1H, s). LRMS: m/z 597 (M+1)+.

Workup

  1. temperatureto cool
  2. customThe resulting mixture was evaporated under reduced pressure
  3. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3d9a4290ba92480bbdead461960a3751
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

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