Potassium Hydroxide → HCID 86586075, compound

HRID 1836230Notes

Reaction equation

HRID 1836230 reaction equation
[NH2:1][C:2]1[NH:7][C:6]2=[N:8][CH:9]=[CH:10][C:5]2=[C:4]([Cl:11])[N:3]=1.[OH-].[K+].COCCOCCN(CCOCCOC)CCOCCOC.[CH2:36]([O:43][C@H:44]1[C@H:48]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C@@H:47]([CH2:57][O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[O:46][CH:45]1Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CC#N>[NH2:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:45]3[O:46][C@H:47]([CH2:57][O:58][CH2:59][C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=4)[C@@H:48]([O:49][CH2:50][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C@@H:44]3[O:43][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 15602668HCID 15602668, compoundHCID 178508434HCID 178508434, compound

Product 1

HCID 86586075HCID 86586075, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 2-amino-4-chloro-1H-pyrrolo[2,3-d]pyrimidine [Liebigs Ann. Chem.1:137 (1983)] (3.03 g, 18 mmol) in anhydrous MeCN (240 mL), powdered KOH (85%; 4.2 g, 60 mmol) and tris[2-(2-methoxyethoxy)-ethyl]amine (0.66 mL, 2.1 mmol) were added and the mixture was stirred at room temperature for 10 min. Then a solution of 2,3,5-tri-O-benzyl-D-arabinofuranosyl bromide [prepared from corresponding 1-O-p-nitrobenzoate (11.43 g, 20.1 mmol) according to Seela et al., J. Org. Chem. (1982), 47, 226] in MeCN (10 mL) was added and stirring continued for another 40 min. Solid was filtered off, washed with MeCN (2×25 mL) and combined filtrate evaporated. The residue was purified on a silica gel column with a solvent system of hexanes/EtOAc:7/1, 6/1 and 5/1. Two main zones were separated. From the more rapidly migrating zone was isolated the α anomer (0.74 g) and from the slower migrating zone the desired β anomer (4.01 g).

Workup

  1. additionwere added
  2. stirringstirring
  3. waitcontinued for another 40 min
  4. filtrationSolid was filtered off
  5. washwashed with MeCN (2×25 mL)
  6. customevaporated
  7. customThe residue was purified on a silica gel column with a solvent system of hexanes/EtOAc
  8. customTwo main zones were separated
  9. customFrom the more rapidly migrating zone was isolated the α anomer (0.74 g)

Sources & evidence

ORD record
ord-35f2de7985f245868b324bf706467332
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

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