Anisole → 2-Chloro-7,7-difluoro-5-methyl-5,7,8,9-tetrahydro-6H-pyrimido[4,5-b][1,4]diazepin-6-one

HRID 1676829Notes

Reaction equation

HRID 1676829 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([F:15])([F:14])[CH2:8][N:7](CC3C=CC(OC)=CC=3)[C:6]=2[N:25]=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([F:15])([F:14])[CH2:8][NH:7][C:6]=2[N:25]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 866375232-Chloro-7,7-difluoro-9-(4-methoxy-benzyl)-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

Product 1

HCID 866375242-Chloro-7,7-difluoro-5-methyl-5,7,8,9-tetrahydro-6H-pyrimido[4,5-b][1,4]diazepin-6-oneYield 12.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 0.3 g (0.0082 mole) of 2-chloro-7,7-difluoro-9-(4-methoxy-benzyl)-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-291) and 0.3 mL of anisole in 10 mL of trifluoroacetic acid was heated at 85 degrees in a pressure tube for 24 hours. The mixture was concentrated under reduced pressure, a small amount of methanol was added followed by ether. The resulting solid was collected by filtration and washed with ether to give 0.26 g of 2-chloro-7,7-difluoro-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-292). as a lightly yellow solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiona small amount of methanol was added
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with ether

Sources & evidence

ORD record
ord-202e5d89cb604be98e9a89e309929b87
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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