Ethylamine → 3-(8-(2,6-difluorophenyl)-2-{[3-(ethylamino)propyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)-4-methyl-N-propylbenzamide

HRID 2243772Notes

Reaction equation

HRID 2243772 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]1[N:7]=[C:8]([C:25]2[CH:26]=[C:27]([CH:34]=[CH:35][C:36]=2[CH3:37])[C:28]([NH:30][CH2:31][CH2:32][CH3:33])=[O:29])[C:9]2[CH2:14][NH:13][C:12](=[O:15])[N:11]([C:16]3[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=3[F:23])[C:10]=2[N:24]=1.[CH2:38]([NH2:40])[CH3:39].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[F:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([F:23])[C:16]=1[N:11]1[C:10]2[N:24]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:40][CH2:38][CH3:39])[N:7]=[C:8]([C:25]3[CH:26]=[C:27]([CH:34]=[CH:35][C:36]=3[CH3:37])[C:28]([NH:30][CH2:31][CH2:32][CH3:33])=[O:29])[C:9]=2[CH2:14][NH:13][C:12]1=[O:15]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 11430Potassium CarbonateHCID 592080253-[2-[(3-chloropropyl)amino]-8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide

Product 1

HCID 592079913-(8-(2,6-difluorophenyl)-2-{[3-(ethylamino)propyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)-4-methyl-N-propylbenzamideYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To 3-[2-[(3-chloropropyl)amino]-8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide (265 mg, 0.50 mmol) in DMF (10 mL) was added ethylamine (1.25 mL, 2.0 M in THF, 2.5 mmol) and potassium carbonate (0.276 g, 2.0 mmol). The mixture was heated at 50° C. for about 20 hours, then at 80° C. for about 4 hours. The mixture was diluted with EtOAc (50 mL), washed with H2O (30 mL+15 mL×2) and brine (20 mL). The organic layers were collected and concentrated. Flash chromatograph afforded the title compound (134 mg, 50%). LC-MS m/z 538 (M+H)+; 1H-NMR (MeOD) δ 0.96-1.02 (m, 6H), 1.61-1.72 (m, 2H), 1.85-1.96 (m, 2H), 2.30 (s, 3H), 3.07 (q, J=7.11 Hz, 2H), 3.19-3.29 (m, 3H), 3.33-3.40 (m, 3H), 3.83 (d, 1H), 3.90 (d, 1H), 6.83-6.99 (m, 3H), 7.51 (d, J=8.03 Hz, 1H), 7.69 (d, J=1.76 Hz, 1H), 7.87 (dd, J=7.91, 1.88 Hz, 1H).

Workup

  1. washwashed with H2O (30 mL+15 mL×2) and brine (20 mL)
  2. customThe organic layers were collected
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0c26a314f16542b39695861d27de11aa
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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