Potassium Iodide → (S)-2-(2-(4-(3-ethylureido)phenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)-N,N-dimethylacetamide

HRID 1697899Notes

Reaction equation

HRID 1697899 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3[CH3:29])[C:16]3[CH2:22][CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].[I-].[K+].Cl[CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35]>CN(C=O)C>[CH2:1]([NH:3][C:4](=[O:5])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3[CH3:29])[C:16]3[CH2:22][CH2:21][N:20]([CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35])[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 758862-chloro-N,N-dimethylacetamideHCID 46913570Urea, N-ethyl-N'-[4-[5,6,7,8-tetrahydro-4-[(3S)-3-Methyl-4-Morpholinyl]pyrido[3,4-d]pyriMidin-2-yl]phenyl]-

Product 1

HCID 59239517(S)-2-(2-(4-(3-ethylureido)phenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)-N,N-dimethylacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.086 mmol), N,N-diisopropylaethylamine (0.26 mmol), potassium iodide (0.06 mmol) were mixed in DMF (0.4 mL), then 2-chloro-N,N-dimethylacetamide was added. The mixture was stirred at room temperature for ˜3 h and the product was purified by reverse-phase HPLC to give the desired product. LC-MS: m/z=+482 (M+H)+.

Workup

  1. customthe product was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-c903939e62d546ef916d8ba234804d50
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

Loading…