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

HRID 1073101Notes

Reaction equation

HRID 1073101 reaction equation
Cl[C:2]1[C:3]2[C:10]([Cl: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]>>[NH2:17][C:2]1[C:3]2[C:10]([Cl: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

3

Reactant 2

HCID 222AmmoniaHCID 3010391HCID 3010391, compound

Product 1

HCID 456428Ethanol, 2-[(4-amino-5-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methoxy]-

Conditions

Temperature
135 °C

Procedure

4,5-Dichloro-7-(2-hydroxyethoxymethyl)pyrrolo[2,3-d]-pyrimidine (7b, 0.07 g) was covered with methanolic-ammonia (20 mL) and heated in a sealed reaction vessel at 135° C. for 10 hours. The solvent was evaporated in vacuo to give a thick syrup. This syrup was subjected to column chromatography and elution of the silica gel column (20×3 cm) with 5% MeOH in CHCl3, which, after evaporation of the appropriate UV absorbing fractions, furnished colorless needles of 10, 0.04 g. (66.6%), mp 149°-150° C. 1H-NMR (DMSO-d6): δ8.14 (s, 1, C2--H), 7.56 (s, 1, C6--H), 6.92 (bs, 2, exchangeable with D2O, NH2), 5.49 (s, 1, N7--CH2), 4.64 (bs, 1, exchangeable with D2O, OH), 3.43 (m, 4, CH2): UVεmax nm (ε33 104): (pH 7) 214 (2.5), 278 (1.3); (pH 1) 233 (2.8), 280 (1.3); (pH 11) 227 (1.4), 278 (1.3). Anal. Calcd. for C9H11N4O2Cl.1/4H2O: C, 43.73; H, 4.66; N, 22.67. Found: C, 43.87; H, 4.36; N. 22.23.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give a thick syrup
  3. washThis syrup was subjected to column chromatography and elution of the silica gel column (20×3 cm) with 5% MeOH in CHCl3, which
  4. customafter evaporation of the appropriate UV
  5. customabsorbing fractions

Sources & evidence

ORD record
ord-b293596eb9c74f59bf024033c0bcb521
Source dataset
uspto-grants-1990_11
Patent number
US04968686

Reaction notes

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