2-Aminophenol → HCID 70345659, compound

HRID 1420314Notes

Reaction equation

HRID 1420314 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])=[C:4]([NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:3]=1.[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[OH:45].N12CCCN=C1CCCCC2>CS(C)=O>[C:26]1([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24][NH:23][C:4]2[N:3]=[C:2]([NH:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[OH:45])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[C@@H:11]2[O:17][C@H:16]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86647542HCID 86647542, compound

Product 1

HCID 70345659HCID 70345659, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1-[2-chloro-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-1-deoxy-N-ethyl-β-D-ribofuranuronamide (0.20 g, 0.038 mmol), 2-aminophenol (0.20 g 1.83 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.052 ml, DBU) and dimethylsulphoxide (1 ml) was stirred and heated at 140° C. under nitrogen for 6 h, and then left at 21° C. overnight. The mixture was partitioned between ethyl acetate (200 ml) and water (40 ml). The aqueous layer was extracted with more ethyl acetate (50 ml) and the total organic solution was washed (water, 20 ml), dried (Na2SO4) and evaporated. The residue was purified on flash silica eluting with dichloromethane:methanol (19:1), and then by preparative TLC (20×20 cm plate with 2 mm layer of Kieselgel 60 F254 ; Art 5717) in dichloromethane:ethyl acetate:ethanol 9:9:2, and then by preparative HPLC (30 to 70% acetonitrile) to give the title compound (0.018 g) as a cream foam, MH+ =596. Analysis found: C, 52.2, H, 4.3, N, 11.8; C32H33N7O5.2CF3CO2H requires C, 52.5, H, 4.3, N, 11.9%

Workup

  1. customThe mixture was partitioned between ethyl acetate (200 ml) and water (40 ml)
  2. extractionThe aqueous layer was extracted with more ethyl acetate (50 ml)
  3. washthe total organic solution was washed (water, 20 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified on flash silica eluting with dichloromethane:methanol (19:1)

Sources & evidence

ORD record
ord-b6a561c28be54875984f90af75eae747
Source dataset
uspto-grants-1999_03
Patent number
US05889178

Reaction notes

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