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

HRID 1801692Notes

Reaction equation

HRID 1801692 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.[CH2:25]([NH2:31])[CH:26]1[O:30][CH2:29][CH2:28][CH2:27]1>CCO>[O:30]1[CH2:29][CH2:28][CH2:27][CH:26]1[CH2:25][NH:31][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 253298TetrahydrofurfurylamineHCID 598566326-(6-chloropyridin-3-yl)-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione

Product 1

HCID 598566296-(6-((Tetrahydrofuran-2-yl)methylamino)pyridin-3-yl)-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dioneYield 82.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
164 °C

Procedure

8a (154 mg) was suspended in tetrahydrofurfurylamine (2.0 g) in EtOH (5 ml) in a pressure tube and stirred at 164° C. for 5 days. After cooling to room temperature, the solid was filtered and washed with methanol to give the product (9b) (150 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid was filtered
  3. washwashed with methanol

Sources & evidence

ORD record
ord-833242f3c19641f7b497ed34068ca53e
Source dataset
uspto-grants-2013_01
Patent number
US08349848B2

Reaction notes

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