Hydrochloric Acid → HCID 136335138, compound

HRID 1824721Notes

Reaction equation

HRID 1824721 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([CH2:13][CH2:14][N:15]1[CH:23]=[N:22][C:21]2[C:16]1=[N:17][C:18]([NH2:25])=[N:19][C:20]=2Cl)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-:27].[Na+]>O1CCCC1>[CH2:1]([O:8][CH2:9][C@@H:10]([CH2:13][CH2:14][N:15]1[CH:23]=[N:22][C:21]2[C:20](=[O:27])[NH:19][C:18]([NH2:25])=[N:17][C:16]1=2)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54040508HCID 54040508, compound

Product 1

HCID 136335138HCID 136335138, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of the chloropurine (13a) (325 mg, 0.9 mmol) in tetrahydrofuran (15 ml) was added hydrochloric acid (2M, 15 ml) and stirred at 60° C. under argon, for 26H. The reaction mixture was cooled in a water bath and sodium hydroxide solution (10M) added until pH9. The aqueous phase was extracted with methanol:ethyl acetate. (7:93, 4×35 ml). The organic phase was dried over sodium sulphate, filtered and evaporated in vacuo to give an oil (150 mg). On standing a white solid crystallised from the aqueous phase which was filtered off, washed with water (5 ml) and diethylether and dried in vacuo to give the title compound (14a) (175 mg, 56.8%). 1H NMR (400 MHz, DMSO-d6) 10.55 (1H, s), 7.66 (1H, s), 7.40 to 7.22 (5H, m), 6.44 (2H, bs), 4.51 (1H, t), 4.42 (2H, t), 4.00 (2H, t), 3.49 to 3.30 (4H, m), 1.76 (2H, q), 1.64 (1H, m). HPLC purity (Method) 98.3%, chiral HPLC (Method D) 89.6% e.e., retention time major peak 10.3 mins, minor peak 6.9 minutes. (C17H11N5O3,−7.7 ppm, NH3Cl) m/z 343.1617. The oil was purified by column chromatography on silica gel eluting with an increasing gradient of methanol (8–22%) in methylene chloride to yield (14a) (87 mg, 28.2%) as an oil.

Workup

  1. temperatureThe reaction mixture was cooled in a water bath
  2. extractionThe aqueous phase was extracted with methanol
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-dd197fabb2b84f818691c5c4cf3234fc
Source dataset
uspto-grants-2006_05
Patent number
US07045525B1

Reaction notes

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