Hydrochloric Acid → HCID 59465203, compound

HRID 1714840Notes

Reaction equation

HRID 1714840 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=O)[C@H:6]([CH3:13])[N:5]([CH2:14][C:15]3[C:20]([CH3:21])=[C:19]([O:22][CH3:23])[C:18]([CH3:24])=[CH:17][N:16]=3)[C:4]=2[N:3]=1.B.C1COCC1.Cl>C1COCC1>[CH3:23][O:22][C:19]1[C:18]([CH3:24])=[CH:17][N:16]=[C:15]([CH2:14][N:5]2[C:4]3[N:3]=[C:2]([NH2:1])[N:11]=[CH:10][C:9]=3[NH:8][CH2:7][C@@H:6]2[CH3:13])[C:20]=1[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 25158232HCID 25158232, compound

Product 1

HCID 59465203HCID 59465203, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(7S)-2-amino-8-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7-methyl-7,8-dihydropteridin-6(5H)-one (Example 1)(164 mg, 0.50 mmol) was stirred in THF (3 mL) and borane-THF complex (1M in THF, 2 mL, 2 mmol) was added slowly. The mixture was stirred at room temperature for 1 hour, then heated at reflux for 30 minutes. The mixture was slowly treated with hydrochloric acid (2M, 5 mL). The solution was loaded onto a SCX column and washed with methanol. The product was eluted with methanolic ammonia (7M) and the volatiles were removed under reduced pressure. Further purification was achieved by MPLC eluting with 5-30% methanol/DCM to give the title compound as a cream foam (115 mg, 73%); 1H NMR spectrum (400 MHz, CDCl3) δ1.22 (3H, d), 2.24 (6H, s), 2.94-2.97 (1H, m), 3.13-3.17 (1H, m), 3.20 (1H, s), 3.57-3.62 (1H, m), 3.75 (3H, s), 4.32 (1H, d), 4.36 (2H, s), 5.59 (1H, d), 7.33 (1H, s), 8.17 (1H, s);

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 minutes
  3. washwashed with methanol
  4. washThe product was eluted with methanolic ammonia (7M)
  5. customthe volatiles were removed under reduced pressure
  6. customFurther purification
  7. washeluting with 5-30% methanol/DCM

Sources & evidence

ORD record
ord-ebc940288f01453392645f67ab02e183
Source dataset
uspto-grants-2010_09
Patent number
US07799781B2

Reaction notes

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