Hydrochloric Acid → Methyl 3-hydroxy-8-methyl-10-(methylamino)-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-d][1,4]diazepine-2-carboxylate

HRID 1012995Notes

Reaction equation

HRID 1012995 reaction equation
[CH2:1]([N:8](C)[CH:9]1[CH2:15][N:14]([CH3:16])[CH2:13][CH2:12][N:11]2[C:17](=[O:26])[C:18]([OH:25])=[C:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=[C:10]12)C1C=CC=CC=1.Cl>CO.[Pd]>[OH:25][C:18]1[C:17](=[O:26])[N:11]2[CH2:12][CH2:13][N:14]([CH3:16])[CH2:15][CH:9]([NH:8][CH3:1])[C:10]2=[N:20][C:19]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57905695HCID 57905695, compound

Product 1

HCID 67316746Methyl 3-hydroxy-8-methyl-10-(methylamino)-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-d][1,4]diazepine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound of Step 1 was dissolved in MeOH and 6 N HCl (2.5 eq.) and stirred overnight under an H2 atmosphere in the presence of 10% Pd/C. The catalyst was then filtered off through celite, and the filtrate was concentrated under reduced pressure and triturated with diethyl ether to yield methyl 3-hydroxy-8-methyl-10-(methylamino)-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-d][1,4]diazepine-2-carboxylate as a yellow solid. MS (ES) C12H18N4O4 requires 282. Found: 283 (M+H+). The crude product was taken in dichloromethane and treated with triethylamine (2.5 eq.) and methyl chloro(oxo)acetate (1.2 eq.). After stirring one hour at room temperature, solvent was removed under reduced pressure and residue was taken in methanol and treated with an excess of dimethyl amine (2 M solution in methanol) at room temperature overnight. Volatiles were evaporated under reduced pressure to the title compound. MS (ES) C16H23N5O6 requires 381. Found: 382 (M+H+).

Workup

  1. filtrationThe catalyst was then filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-906988f7ca504779a52771e2a79faf56
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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