Ammonia → Ethanol, 2-[(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methoxy]-

HRID 1651084Notes

Reaction equation

HRID 1651084 reaction equation
Cl[C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][OH:16])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:17]>CO>[NH2:17][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][OH:16])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 3010393HCID 3010393, compound

Product 1

HCID 456429Ethanol, 2-[(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methoxy]-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

4-Chloro-5-iodo-7-(2-hydroxyethoxymethyl)pyrrolo[2,3-d] pyrimidine (9b, 0.3 g) was covered with methanol saturated with ammonia (25 mL) and the reaction mixture was heated at 130 degrees C. in a sealed vessel for 10 hours. The solvent was concentrated in vacuo to give a semi-solid mass which was recrystallized from methanol to afford 12, 0.20 g (71.4%), mp 169-170 degrees C. 1H NMR (DMSO-d6): δ 8.7 (s, 1, C2-H), 8.3 (s, 1, C6-H), 5.7 (s, 2, N7-CH2) 4.6 (t, 1, J=4H3, exchangeable with D2O, OH): UVλmax nm(ε×104); (pH 7) 210 (2.0), 280 (0.9); (pH 1) 230 (1.8), 279 (0.9); (pH 11) 228 (0.9), 278 (0.9).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customto give a semi-solid mass which
  3. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-3962c8295b354560b6337dea97ecd143
Source dataset
uspto-grants-1990_05
Patent number
US04927830

Reaction notes

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