Ammonia → 4-Amino-7-(3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-fluoromethyl-beta-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 2212937Notes

Reaction equation

HRID 2212937 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[Cl:37])[C@@H:14]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=4[Cl:24])[C@@:12]3([CH2:38][F:39])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:40]>O1CCOCC1>[NH2:40][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[Cl:37])[C@@H:14]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=4[Cl:24])[C@@:12]3([CH2:38][F:39])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 872853684-Chloro-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c-fluoromethyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 210500814-Amino-7-(3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-fluoromethyl-beta-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
-78 °C

Procedure

The compound from Step A (18 mg, 0.03 mmol) was dissolved in the minimum amount of 1,4-dioxane and placed in a stainless steel bomb. The bomb was cooled to −78° C. and liquid ammonia was added. The bomb was sealed and heated at 90° C. for 24 h. The ammonia was allowed to evaporate and the residue concentrated to a white solid which was used in the next step without further purification.

Workup

  1. customThe bomb was sealed
  2. temperatureheated at 90° C. for 24 h
  3. customto evaporate
  4. concentrationthe residue concentrated to a white solid which
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-01945ce81542499899401fd3eac7b02b
Source dataset
uspto-grants-2006_09
Patent number
US07105499B2

Reaction notes

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