2-Methoxyethylamine → 6-(6-(2-methoxyethylamino)pyridin-3-yl)-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione

HRID 1801690Notes

Reaction equation

HRID 1801690 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[NH:16][C:15]3[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][CH3:24])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH3:25][O:26][CH2:27][CH2:28][NH2:29]>CCO>[CH3:25][O:26][CH2:27][CH2:28][NH:29][C:2]1[N:7]=[CH:6][C:5]([C:8]2[NH:16][C:15]3[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][CH3:24])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 598566326-(6-chloropyridin-3-yl)-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione

Product 1

HCID 598566356-(6-(2-methoxyethylamino)pyridin-3-yl)-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dioneYield 56.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
164 °C

Procedure

8a (100 mg) was suspended in methoxyethylamine (1.5 g), in EtOH (4 mL) in a pressure tube and stirred at 164° C. for 28 hrs. After cooling to room temperature, the solvent was removed and the solid was purified by column (26 g silica gel, RT Scientific) (CH2Cl2:MeOH=100:0 to 97:3). The fractions were evaporated and washed with ether to give the product 9a (63 mg). The mother liquid was evaporated and afforded another 30 mg of the product.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed
  3. customthe solid was purified by column (26 g silica gel, RT Scientific) (CH2Cl2:MeOH=100:0 to 97:3)
  4. customThe fractions were evaporated
  5. washwashed with ether

Sources & evidence

ORD record
ord-93f254bf760147f0954078fa4a75616a
Source dataset
uspto-grants-2013_01
Patent number
US08349848B2

Reaction notes

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