1,4-Dibromobutane → HCID 178526819, compound

HRID 1819413Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:31])([F:30])[F:29])[N:11]=2)[CH2:4][CH2:3]1.Br[CH2:33][CH2:34][CH2:35][CH2:36]Br.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[N+:16]([C:15]1[C:10]([NH:9][CH2:8][C@H:5]2[CH2:4][CH2:3][C@H:2]([N:1]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[CH2:7][CH2:6]2)=[N:11][C:12]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][C:28]([F:30])([F:31])[F:29])=[N:13][CH:14]=1)([O-:18])=[O:17]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of N4-[(trans-4-aminocyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]-pyrimidine-2,4-diamine (86 mg, 0.2 mmol) in DMF (1 mL) were added 1,4-dibromobutane (710 μL, 0.59 mmol) and DIPEA (103 μL, 0.59 mmol). The reaction mixture was stirred at 65° C. for 4 h. The reaction mixture was then diluted with EtOAc and washed with saturated NaHCO3 and water (×4). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel preparative TLC using 10:1:0.05 CH2Cl2:MeOH:NH4OH as an eluent to afford 60 mg (62%) of the title compound as an off-white solid, m/z 493.3 [M−1]+.

Workup

washwashed with saturated NaHCO3 and water (×4)
dry with materialThe organic phase was dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record: ord-1cfd4d72854245ef8bdd06531a80a314
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601714B2

Reaction notes

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