Allylamine → N-allyl-2-chloro-7-(4-fluorophenyl)-7-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine

HRID 474273Notes

Reaction equation

HRID 474273 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][CH2:9][C:8]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)([CH3:11])[C:6]=2[N:7]=1.CCN(C(C)C)C(C)C.[CH2:29]([NH2:32])[CH:30]=[CH2:31]>C(Cl)Cl>[CH2:29]([NH:32][C:4]1[C:5]2[CH2:10][CH2:9][C:8]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)([CH3:11])[C:6]=2[N:7]=[C:2]([Cl:1])[N:3]=1)[CH:30]=[CH2:31]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 81531DiisopropylethylamineHCID 580758222,4-Dichloro-7-(4-fluorophenyl)-7-methyl-6,7-dihydro-5H-cyclopenta[D]pyrimidine

Product 1

HCID 86668117N-allyl-2-chloro-7-(4-fluorophenyl)-7-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amineYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-dichloro-7-(4-fluorophenyl)-7-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (Preparation U, 1.00 g, 3.37 mmol) in DCM (13.46 mL) was added DIPEA (1.176 ml, 6.73 mmol), then allylamine (0.303 ml, 4.04 mmol). The reaction solution was allowed to stir at rt. The reaction was concentrated in vacuo. The residue was applied to silica gel and eluted with a 0 to 50% EtOAc/Hexane gradient to afford N-allyl-2-chloro-7-(4-fluorophenyl)-7-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (896.2 mg, 2.82 mmol, 84% yield) as a white solid. LC-MS (M+H)+=316.2. 1H NMR (500 MHz, CDCl3) δ ppm 7.18-7.23 (2H, m), 6.91-6.98 (2H, m), 5.90-6.00 (1H, m), 5.26 (1H, dd, J=17.2, 1.4 Hz), 5.20 (1H, dd, J=10.1, 1.2 Hz), 4.62 (1H, br. s), 4.17 (1H, td, J=5.7, 1.7 Hz), 2.56-2.62 (2H, m), 2.43-2.50 (1H, m), 2.19-2.28 (1H, m), 1.63 (3H, s).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washeluted with a 0 to 50% EtOAc/Hexane gradient

Sources & evidence

ORD record
ord-203b39ef882b482f96eb1e5f734bae23
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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