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 2377727Notes

Reaction equation

HRID 2377727 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-217d718527ba4638a7f37b1f76d32a40
Source dataset
uspto-grants-2008_12
Patent number
US07470697B2

Reaction notes

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