Triethylamine → 3-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)-N-(2,2-dimethylpropyl)-4-methylbenzamide

HRID 2243745Notes

Reaction equation

HRID 2243745 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22]([OH:24])=O)[C:13]=2[CH2:12][NH:11][C:10]1=[O:35].[CH3:36][C:37]([CH3:41])([CH3:40])[CH2:38][NH2:39].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22]([NH:39][CH2:38][C:37]([CH3:41])([CH3:40])[CH3:36])=[O:24])[C:13]=2[CH2:12][NH:11][C:10]1=[O:35]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 79882NeopentylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57530538HCID 57530538, compound

Product 1

HCID 592081143-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)-N-(2,2-dimethylpropyl)-4-methylbenzamideYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of 3-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]-amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)-4-methylbenzoic acid (30 mg, 0.062 mmol) in dichloromethane (2.0 mL) and DMF (0.5 mL) were added (2,2-dimethylpropyl)amine (10.9 μL, 0.093 mmol), HBTU (25.6 mg, 0.068 mmol) and triethylamine (35.0 μL, 0.25 mmol). The reaction mixture was stirred at room temperature for 16 hours then was applied to HPLC to afford the titled compound 14.9 mg (44%). LC-MS m/z 552 (M+H)+; 1H-NMR (MeOD) 0.99 (s, 9H), 2.33 (s, 3H), 2.76 (s, 6H), 3.15 (s, 2H), 3.24 (s, 2H), 3.54 (m, 2H), 4.16 (m, 2H), 7.18 (m, 2H), 7.51 (m, 2H), 7.72 (s, 1H), 7.89 (m, 1H).

Sources & evidence

ORD record
ord-17af8b2427524f0888fb2a0b33efd661
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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