1-Tert-butyl-4-isocyanatobenzene → 1-((3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)methyl)-3-(4-(tert-butyl)phenyl)urea

HRID 511586Notes

Reaction equation

HRID 511586 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:6][CH:5]([N:7]([CH2:9][C@@H:10]2[C@H:14]3[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]3[C@H:12]([N:20]3[CH:28]=[N:27][C:26]4[C:21]3=[N:22][CH:23]=[N:24][C:25]=4[NH2:29])[O:11]2)[CH3:8])[CH2:4]1.[C:30]([C:34]1[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[O:42])=[CH:36][CH:35]=1)([CH3:33])([CH3:32])[CH3:31]>C(Cl)Cl>[NH2:29][C:25]1[N:24]=[CH:23][N:22]=[C:21]2[C:26]=1[N:27]=[CH:28][N:20]2[C@H:12]1[C@@H:13]2[O:17][C:16]([CH3:19])([CH3:18])[O:15][C@@H:14]2[C@@H:10]([CH2:9][N:7]([CH3:8])[CH:5]2[CH2:4][CH:3]([CH2:2][NH:1][C:41]([NH:40][C:37]3[CH:38]=[CH:39][C:34]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:35][CH:36]=3)=[O:42])[CH2:6]2)[O:11]1

Participants

4

Reactant 2

HCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 677761929-((3aR,4R,6R,6aR)-6-(((3-(aminomethyl)cyclobutyl)(methyl)amino)methyl)-2,2-dimethyltetrahydro furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine

Product 1

HCID 677761471-((3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)methyl)-3-(4-(tert-butyl)phenyl)ureaYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-((3aR,4R,6R,6aR)-6-(((3-(aminomethyl)cyclobutyl)(methyl)amino)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine in DCM (4 ml) was added 1-tert-butyl-4-isocyanatobenzene (37 mg). The mixture was stirred at RT for 1 h. The mixture was concentrated and purified via preparative-TLC (DCM:MeOH=10:1) to give the title compound (55 mg, Yield 45% for two steps). ESI-MS (m/z): 578.3[M+1]+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified via preparative-TLC (DCM:MeOH=10:1)

Sources & evidence

ORD record
ord-33cbde51ff934e158e3e70b826f217d8
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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