Ammonia → HCID 3010393, compound

HRID 1651081Notes

Reaction equation

HRID 1651081 reaction equation
[I:1]Cl.[Cl:3][C:4]1[C:5]2[CH:12]=[CH:11][N:10]([CH2:13][O:14][CH2:15][CH2:16][O:17]C(=O)C)[C:6]=2[N:7]=[CH:8][N:9]=1.CO.N>C(Cl)Cl>[Cl:3][C:4]1[C:5]2[C:12]([I:1])=[CH:11][N:10]([CH2:13][O:14][CH2:15][CH2:16][OH:17])[C:6]=2[N:7]=[CH:8][N:9]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 24640Iodine chlorideHCID 14221930HCID 14221930, compound

Product 1

HCID 3010393HCID 3010393, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodine monochloride (0.38 mL) was added dropwise with stirring under a nitrogen atmosphere to a solution of 4-chloro-7-(2-acetoxyethoxymethyl)pyrrolo[2,3-d]pyrimidine (3, 0.82 g) in dry CH2Cl2 (25 mL). The reaction mixture was stirred at room temperature for 20 hours. The solvent was evaporated at 40 degrees C. under high pressure and the dark purple syrup was placed on the top of a silica gel column. Elution of the column (15×2 cm) with CHCl3 yielded a dark colored syrup, after evaporation of the appropriate UV absorbing fractions, which on trituration with dry ether gave a crystalline product. (0.3 g) as colorless needles. These needles were covered with methanol saturated with ammonia (30 mL) at 0 degrees C., and the reaction mixture stirred at room temperature in a pressure bottle for 20 hours. The solvent was evaporated under high vacuum and the resulting solid was recrystallized from methanol to furnish colorless needles of 9b, 0.21 g (80.75%), mp 154- 155 degrees C. 1H-NMR (DMSO-d6): 8.69 (s, 1, C2-H), 8.14 (s, 1, C6-H), 5.66 (s, 2, N7-CH2), 4.57 (t, 1, J=3.0 Hz, 3.3 Hz, exchangeable with D2O, OH), 3.46-3.33 (m, 4, CH2): UVλmax nm (ε×104); (pH 7) 225 (1.8), 296 (0.9); (pH 1) 233 (2.1), 280 (0.95); (pH 11) 228 (0.8), 280 (0.85).

Workup

  1. customThe solvent was evaporated at 40 degrees C
  2. washElution of the column (15×2 cm) with CHCl3
  3. customyielded a dark colored syrup
  4. customafter evaporation of the appropriate UV
  5. customabsorbing fractions, which on trituration with dry ether
  6. customgave a crystalline product
  7. stirring, and the reaction mixture stirred at room temperature in a pressure bottle for 20 hours
  8. customThe solvent was evaporated under high vacuum
  9. customthe resulting solid was recrystallized from methanol

Sources & evidence

ORD record
ord-5a3315f35b504996a191170ca64919c8
Source dataset
uspto-grants-1990_05
Patent number
US04927830

Reaction notes

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