1-N,2-N-dimethylcyclohexane-1,2-diamine → HCID 86731168, compound

HRID 920675Notes

Reaction equation

HRID 920675 reaction equation
[CH2:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]2[NH:14][CH:13]=[C:12]([CH:15]3[CH2:20][CH2:19][CH:18]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:17][CH2:16]3)[C:10]=2[N:11]=1)[CH2:2][CH2:3][CH3:4].I[C:30]1[CH:42]=[CH:41][C:33]([CH2:34][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[CH:32][CH:31]=1.CNC1CCCCC1NC>CN1C(=O)CCC1.CCOC(C)=O.[Cu]I>[CH2:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]2[N:14]([C:30]3[CH:31]=[CH:32][C:33]([CH2:34][N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)=[CH:41][CH:42]=3)[CH:13]=[C:12]([CH:15]3[CH2:16][CH2:17][CH:18]([O:21][Si:22]([C:25]([CH3:27])([CH3:26])[CH3:28])([CH3:23])[CH3:24])[CH2:19][CH2:20]3)[C:10]=2[N:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 27955004-(4-Iodobenzyl)morpholineHCID 86731169HCID 86731169, compound

Product 1

HCID 86731168HCID 86731168, compoundYield 100.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
195 °C

Procedure

A solution of N-butyl-7-(4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-5H-pyrrolo[3,2-d]pyrimidin-2-amine (59 mg, 0.14653 mmol) and 4-iodobenzyl morpholine (67 mg, 0.22 mmol) in NMP (1 mL) was added CuI (3 mg, 0.022 mmol) and N,N′-dimethylcyclohexane-1,2-diamine (2 mg, 0.044 mmol). The reaction mixture was stirred under microwave irradiation at 195° C. for 30 min. Then the reaction was diluted with EtOAc. The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by ISCO to provide the desired product (85 mg, 99%). 1H NMR (400 MHz, CDCl3) δ 8.48 (s, 1H), 7.36 (d, J=8 Hz, 2H), 7.25 (d, J=8 Hz, 2H), 7.17 (s, 1H), 4.86 (s, 1H), 3.71-3.52 (m, 4H), 3.44-3.38 (m, 4H), 3.32-3.17 (m, 1H), 2.81-2.71 (m, 2H), 2.45-2.33 (m, 4H), 2.15-2.04 (m, 2H), 1.96-1.83 (m, 2H), 1.61-1.29 (m, 8H), 0.94-0.75 (m, 12H), 0.00 (s, 6H). MS m/z 578.4 [M+H]+.

Workup

  1. dry with materialThe organic layer was dried (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by ISCO

Sources & evidence

ORD record
ord-b5c9b00bbef540ff8fbda56cb39c9359
Source dataset
uspto-grants-2016_03
Patent number
US09273056B2

Reaction notes

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