1,1'-Carbonyldiimidazole → 9-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-7H-purin-8(9H)-one

HRID 1363247Notes

Reaction equation

HRID 1363247 reaction equation
[Si:1]([O:18][C@H:19]1[C:28]2[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=2)[C@H:22]([NH:30][C:31]2[C:36]([NH2:37])=[CH:35][N:34]=[C:33]([N:38]3[C:42]4[CH:43]=[C:44]([F:47])[CH:45]=[CH:46][C:41]=4[N:40]=[CH:39]3)[N:32]=2)[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN([C:53](N2C=NC=C2)=[O:54])C=1>C1COCC1>[Si:1]([O:18][C@H:19]1[C:28]2[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=2)[C@H:22]([N:30]2[C:53](=[O:54])[NH:37][C:36]3[C:31]2=[N:32][C:33]([N:38]2[C:42]4[CH:43]=[C:44]([F:47])[CH:45]=[CH:46][C:41]=4[N:40]=[CH:39]2)=[N:34][CH:35]=3)[CH2:21][CH2:20]1)([C:14]([CH3:16])([CH3:15])[CH3:17])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59846398N4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)pyrimidine-4,5-diamine

Product 1

HCID 598463719-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-7H-purin-8(9H)-oneYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)pyrimidine-4,5-diamine (490 mg, 0.751 mmol, 1 equiv) was dissolved in anhydrous THF (15 mL) and CDI (737 mg, 4.54 mmol, 7 equiv) was added. The reaction was stirred at RT under argon overnight. The solvent was removed by evaporation. The residue was dissolved in EtOAc (30 mL) and washed with saturated NaHCO3, water and brine, dried (Na2SO4). The organic layer was evaporated to dryness. The residue was applied to ISCO (12 g column, MeOH—CH2Cl2 0-2%) to give a white solid product (420 mg, 82%). MS (ESI): 673.3

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in EtOAc (30 mL)
  3. washwashed with saturated NaHCO3, water and brine
  4. dry with materialdried (Na2SO4)
  5. customThe organic layer was evaporated to dryness

Sources & evidence

ORD record
ord-e27c0e87768c4ddf841637db9f15d25f
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

Loading…