2-Chloro-N,N-dimethylethylamine → HCID 58981183, compound

HRID 1181798Notes

Reaction equation

HRID 1181798 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH3:6])[CH3:5].C(N(CC)CC)C.C1CCN2C(=NCCC2)CC1.[CH3:25][N:26]1[C:31](=[O:32])[C:30]2=[C:33]([C:47]3[CH:52]=[CH:51][N:50]=[CH:49][CH:48]=3)[N:34]([CH2:36][C:37]3[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH:40]=[CH:39][CH:38]=3)[N:35]=[C:29]2[NH:28][C:27]1=[O:53]>CS(C)=O.CN(C)C=O>[CH3:5][N:4]([CH3:6])[CH2:3][CH2:2][N:28]1[C:29]2=[N:35][N:34]([CH2:36][C:37]3[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH:40]=[CH:39][CH:38]=3)[C:33]([C:47]3[CH:52]=[CH:51][N:50]=[CH:49][CH:48]=3)=[C:30]2[C:31](=[O:32])[N:26]([CH3:25])[C:27]1=[O:53]

Participants

7

Reactant 4

HCID 79012-Chloro-N,N-dimethylethylamineHCID 8471TriethylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1363341135-methyl-2-(1-naphthylmethyl)-3-(4-pyridinyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 58981183HCID 58981183, compoundYield 158.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

N-(2-Chloroethyl)-N,N-dimethylamine hydrichloride (0.058 g), followed by triethylamine (0.092 mL) and DBU (0.103 mL), were added to a solution of 5-methyl-2-(1-naphthylmethyl)-3-(4-pyridinyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (0.064 g) in 3:1 dimethylformamide and DMSO (1 mL). The mixture was heated at 90° C. for 18 h then cooled to room temperature. Crude reaction was purified on preparative HPLC to give the title compound (0.120 g). Mass 455.03 (M+H).

Workup

  1. temperaturethen cooled to room temperature
  2. customCrude reaction
  3. customwas purified on preparative HPLC

Sources & evidence

ORD record
ord-4bb78ebc9e764b0db249188a47de1cc5
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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