1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-chloro-2-(4-methoxy-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

HRID 657730Notes

Reaction equation

HRID 657730 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[CH2:12][NH:11][CH2:10][CH2:9][C:5]=2[N:6]=[CH:7][N:8]=1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17](F)=[C:18]([CH:21]=1)[C:19]#[N:20].N12CCCN=C1CCCCC2>C(Cl)Cl>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([N:11]2[CH2:10][CH2:9][C:5]3[N:6]=[CH:7][N:8]=[C:3]([O:2][CH3:1])[C:4]=3[CH2:12]2)=[C:18]([CH:21]=1)[C:19]#[N:20]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 936535-Chloro-2-fluorobenzonitrileHCID 509892144-methoxy-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine

Product 1

HCID 598406855-chloro-2-(4-methoxy-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrileYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (12.88 g, 0.078 mol), 5-chloro-2-fluorobenzonitrile (40 g, 0.2 mol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (60 mL, 0.4 mol) was heated at 80° C. for 3 hours. After cooling the mixture was diluted with CH2Cl2 (300 mL), washed with water, dried, and concentrated to afford a brown solid which was purified by silica gel chromatography (0-50% EtOAc/hexane) to afford a solid (19.33 g, 78.3%).

Workup

  1. temperatureAfter cooling the mixture
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customto afford a brown solid which
  6. customwas purified by silica gel chromatography (0-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-78b29e5dfb8148d7b68442a6bb50ff63
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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