Diisopropylethylamine → HCID 86668108, compound

HRID 474256Notes

Reaction equation

HRID 474256 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.C(N(C(C)C)CC)(C)C.[NH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33]1[CH:40]=[C:39]([N+:41]([O-:43])=[O:42])[CH:38]=[CH:37][C:34]=1[C:35]#[N:36]>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:40]=[C:39]([N+:41]([O-:43])=[O:42])[CH:38]=[CH:37][C:34]=2[C:35]#[N:36])[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 580754632,4-Dichloro-7-phenyl-6,7-dihydro-5H-cyclopenta[D]pyrimidineHCID 66665806HCID 66665806, compound

Product 1

HCID 86668108HCID 86668108, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,4-dichloro-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (Preparation of R, 1.1 g, 4.163 mmol) in acetonitrile (40 mL) was added diisopropylethylamine (0.807 g, 6.245 mmol) followed by 2-(4-aminobutoxy)-4-nitrobenzonitrile (Preparation O, 1.174 g, 4.99 mmol) at room temperature. The reaction mixture was stirred at rt for 18 h. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane (10 mL) and silica (2 g). The resultant slurry of the compound on silica was subjected to flash chromatography using a Teledyne Isco instrument (12 g RediSep silica column, with 50% ethyl acetate in pet-ether) to get 2-(4-(2-chloro-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ylamino)butoxy)-4-nitrobenzonitrile (0.9 g, 47%) as a light yellow solid. LC-MS (M+H)+=464.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.08 (1H, d, J=8.4 Hz), 7.98 (1H, s), 7.91 (1H, d, J=8.8 Hz), 7.57 (1H, m), 7.32-7.13 (5H, m), 4.39-4.35 (2H, t, J=6.4 Hz), 4.19-4.15 (1H, t, J=8.0 Hz), 3.46-3.33 (2H, m), 2.85-2.75 (1H, m), 2.60-2.50 (2H, m), 1.99-1.00 (1H, m), 1.88-1.75 (4H, m).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d38b45d29e08499eb0581998f8548d1d
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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