Dimethylformamide → HCID 68152124, compound

HRID 2047633Notes

Reaction equation

HRID 2047633 reaction equation
[CH:1]1([N:6]2[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][NH:9][C:8]3[CH:15]=[N:16][C:17]([NH:19][C:20]4[CH:21]([C:25](=O)[CH:26]=[CH:27][C:28]=4[O:29][CH3:30])C([O-])=O)=[N:18][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:32](=[O:35])([O-])[O-:33].[Cs+].[Cs+].[CH3:38]I.CN([CH:43]=[O:44])C>C(OC(=O)C)C>[CH:1]1([N:6]2[CH2:12][C:11]([CH3:13])([CH3:14])[C:43](=[O:44])[N:9]([CH3:10])[C:8]3[CH:15]=[N:16][C:17]([NH:19][C:20]4[CH:21]=[CH:25][C:26]([C:32]([O:33][CH3:38])=[O:35])=[CH:27][C:28]=4[O:29][CH3:30])=[N:18][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86672898HCID 86672898, compound

Product 1

HCID 68152124HCID 68152124, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-(9-cyclopentyl-7,7-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepine-2-ylamino-3-methoxybenzoate and dicesium carbonate (118.6 mg, 0.3640 mmol) were mixed in DMF. MeI (103.3 mg, 45.31 μL, 0.7280 mmol) was then added and the reaction mixture was stirred at room temperature overnight. The mixture was diluted with ethylacetate, filtered through small pad of celite, washed twice with water, dried and concentrated to a yellow solid. Purification by flash chromatography on silica gel, eluting with 1% methanol/DCM, gave methyl 4-(9-cyclopentyl-5,7,7-trimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzoate as a pale yellow solid (47 mg, 56%). NMR CDCl3 1.25 (6H, s), 1.53-1.58 (2H, m), 1.69-1.83 (4H, m), 2.02-2.08 (2H, m), 3.33 (3H, s), 3.4 (2H, s), 3.92 (3H, s), 3.98 (3H, s), 5.27-5.34 (1H, m), 7.23-7.26 (1H, brs), 7.55 (1H, s), 7.72-7.77 (2H, m), 7.88 (1H, s), 8.56 (1H, d); MS (ES+) 454.1 (ES−) 452.1

Workup

  1. filtrationfiltered through small pad of celite
  2. washwashed twice with water
  3. customdried
  4. concentrationconcentrated to a yellow solid
  5. customPurification by flash chromatography on silica gel
  6. washeluting with 1% methanol/DCM

Sources & evidence

ORD record
ord-5eb365b22a804094a65f51e1a6242993
Source dataset
uspto-grants-2013_11
Patent number
US08592577B2

Reaction notes

Loading…