Triethylamine → Methyl (4-{[[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl](3-piperidin-1-ylpropyl)amino]methyl}phenyl)acetate

HRID 339942Notes

Reaction equation

HRID 339942 reaction equation
C(O)(=O)/C=C\C(O)=O.C(O)(=O)/C=C\C(O)=O.[NH2:17][C:18]1[N:26]=[C:25]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])[N:24]=[C:23]2[C:19]=1[NH:20][C:21](=[O:45])[N:22]2[CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:67]([C:69]1[CH:74]=[CH:73][C:72]([CH2:75][C:76]([O:78][CH3:79])=[O:77])=[CH:71][CH:70]=1)=O.C([O-])([O-])=O.[Na+].[Na+]>CN1C(=O)CCC1.O>[NH2:17][C:18]1[N:26]=[C:25]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])[N:24]=[C:23]2[C:19]=1[NH:20][C:21](=[O:45])[N:22]2[CH2:32][CH2:33][CH2:34][N:35]([CH2:67][C:69]1[CH:70]=[CH:71][C:72]([CH2:75][C:76]([O:78][CH3:79])=[O:77])=[CH:73][CH:74]=1)[CH2:36][CH2:37][CH2:38][N:39]1[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 19363032Methyl 2-(4-formylphenyl)acetateHCID 1317320776-amino-2-butoxy-9-{3-[(3-piperidin-1-ylpropyl)amino]propyl}-7,9-dihydro-8H-purin-8-one dimaleate

Product 1

HCID 67989365Methyl (4-{[[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl](3-piperidin-1-ylpropyl)amino]methyl}phenyl)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent3×

Conditions

Temperature
25 °C

Procedure

A mixture of 6-amino-2-butoxy-9-{3-[(3-piperidin-1-ylpropyl)amino]propyl}-7,9-dihydro-8H-purin-8-one dimaleate (20.0 g, 31.3 mmol), triethylamine (9.5 g, 94.1 mmol) and NMP (72 g) was stirred at 25° C. for 30 min. Sodium triacetoxyborohydride (11.3 g, 53.3 mmol) was added to the solution and stirred for 15 min. A solution of methyl (4-formylphenyl)acetate (8.4 g, 47.1 mmol) in NMP (10.3 g g) was added to the solution and the mixture stirred for 8 hr. Then NMP (41 g) was poured into the reaction solution and cooled to 5° C. To the solution was added cold water (200 g) dropwise and the mixture stirred. The reaction mixture was adjusted to pH9 by using 10% aqueous Na2CO3 and water (86 g) added. After stirring for 1 hr, the reaction mixture was filtered, the collecting solid washed with cooled water and dried to give the crude subtitle compound as a white solid. Yield 15.0 g, 84%.

Workup

  1. stirringstirred for 15 min
  2. stirringthe mixture stirred for 8 hr
  3. temperaturecooled to 5° C
  4. stirringthe mixture stirred
  5. additionadded
  6. stirringAfter stirring for 1 hr
  7. filtrationthe reaction mixture was filtered
  8. washthe collecting solid washed with cooled water
  9. customdried

Sources & evidence

ORD record
ord-99505246748c4273a6f7c680e3f9d602
Source dataset
uspto-grants-2014_11
Patent number
US08895570B2

Reaction notes

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