Tetrahydrofuran → HCID 58222541, compound

HRID 2063380Notes

Reaction equation

HRID 2063380 reaction equation
[CH:1]1([C:4]2[N:5]([CH2:29][CH3:30])[C:6]3[C:11]([N:12]=2)=[C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@@H:14]2[CH3:19])[N:9]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)[N:7]=3)[CH2:3][CH2:2]1.C1COCC1>CO.[Pd]>[CH:1]1([C:4]2[N:5]([CH2:29][CH3:30])[C:6]3[C:11]([N:12]=2)=[C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@@H:14]2[CH3:19])[N:9]=[C:8]([C:20]2[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=2)[N:7]=3)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 58222537HCID 58222537, compound

Product 1

HCID 58222541HCID 58222541, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (S)-4-(8-cyclopropyl-9-ethyl-2-(4-nitrophenyl)-9H-purin-6-yl)-3-methylmorpholine (76.0 mg, 0.186 mmol) dissolved in anhydrous methanol (3.0 mL) and anhydrous THF (4.6 mL) was subjected to a continuous flow hydrogenated apparatus (H-Cube: 10% Pd/C cartridge, 1.0 mL/min flow). The crude was concentrated in vacuo and purified by column chromotagraphy (Si-PPC, gradient 20 to 100% ethyl acetate in heptane) to give the desired product as a white solid (52.0 mg, 73.8%). 1H NMR (CDCl3, 500 MHz) δ ppm 8.28 (d, J=8.5 Hz, 2H), 6.73 (d, J=8.6 Hz, 2H), 5.47 (broad s, 1H), 5.17 (broad s, 1H), 4.40 (broad s, 2H), 4.03 (dd, J=11.3 Hz, 3.3 Hz, 1H), 3.89 to 3.77 (m, 2H), 3.68 (td, J=12.0 Hz, 2.8 Hz, 1H), 3.50 (t, J=11.7 Hz, 1H), 2.02 to 1.91 (m, 1H), 1.48 (t, J=7.2 Hz, 3H), 1.39 (d, J=6.8 Hz, 3H), 1.33 to 1.22 (m, 2H), 1.20 to 1.10 (m, 2H), 1.06 (dd, J=8.0 Hz, 3.1 Hz, 2H); LC-MS m/z (method A)=379.3 [M+H]+, RT=1.96 min.

Workup

  1. concentrationThe crude was concentrated in vacuo
  2. custompurified by column chromotagraphy (Si-PPC, gradient 20 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-1f39753aac2649f680a4b5b4e8f5d643
Source dataset
uspto-grants-2012_10
Patent number
US08288381B2

Reaction notes

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