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

HRID 2234403Notes

Reaction equation

HRID 2234403 reaction equation
Br[C:2]1[C:3]([N:9](CC2C=C(OC)C=C(OC)C=2)[CH2:10][CH2:11][C:12]([NH:14][CH3:15])=[O:13])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:8][C:5]1[N:4]=[C:3]2[C:2]([N:14]([CH3:15])[C:12](=[O:13])[CH2:11][CH2:10][NH:9]2)=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 866175753-[(5-bromo-2-chloro-pyrimidin-4-yl)-[(3,5-dimethoxyphenyl)methyl]amino]-N-methyl-propanamide2×

Product 1

HCID 866175762-Chloro-5-methyl-5,7,8,9-tetrahydro-6H-pyrimido[4,5-b][1,4]diazepin-6-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-[(5-bromo-2-chloro-pyrimidin-4-yl)-[(3,5-dimethoxyphenyl)methyl]amino]-N-methyl-propanamide (Intermediate 97; 83 mg, 0.23 mmol) was taken up in DCM (1 mL) and TFA (1 mL) and stirred for 30 minutes. A further addition of TFA (1 mL) was made and stirring continued overnight. The reaction mixture was diluted with DCM (25 mL) and poured directly onto a SCX-3 cartridge (2 g). The cartridge was washed through with methanol (50 mL). Products were eluted with 2M ammonia in methanol and ammoniacal eluant evaporated to dryness to afford the title compound as an off white solid (34 mg, 70%)

Workup

  1. additionpoured directly onto a SCX-3 cartridge (2 g)
  2. washThe cartridge was washed through with methanol (50 mL)
  3. washProducts were eluted with 2M ammonia in methanol and ammoniacal eluant
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-3f94e51438654b5fbdb567396152f26a
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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