N,N'-Dimethylethylenediamine → HCID 56932316, compound

HRID 595003Notes

Reaction equation

HRID 595003 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][N:6]1[C:10]2=[N:11][C:12]([NH:15][C:16]3[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=3)=[N:13][CH:14]=[C:9]2[CH:8]=[N:7]1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][C:26]1=[O:31].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>O1CCOCC1.[Cu](I)I>[CH3:21][N:19]1[CH:20]=[C:16]([NH:15][C:12]2[N:11]=[C:10]3[N:6]([CH2:5][C:4]4[CH:3]=[C:2]([N:25]5[CH2:30][CH2:29][O:28][CH2:27][C:26]5=[O:31])[CH:24]=[CH:23][CH:22]=4)[N:7]=[CH:8][C:9]3=[CH:14][N:13]=2)[CH:17]=[N:18]1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 669533-MorpholinoneHCID 66765269HCID 66765269, compound

Product 1

HCID 56932316HCID 56932316, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(3-iodobenzyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (50 mg, 0.12 mmol) in dioxane (1 mL) were added morpholin-3-one (15 mg, 1.25 eq), copper iodide (4.4 mg, 0.2 eq), potassium phosphate (49 mg, 2 eq) and N,N′-dimethylethylene diamine (5 μl, 0.4 eq). After stirring for 16 h at 90° C., the reaction mixture was partitioned between 0.5M EDTA and DCM. The aqueous phase was extracted with DCM, the combined organic phases dried over sodium sulfate and evaporated. The residue was purified by preparative HPLC to yield the title compound (23 mg, 56 μmol, 47%). 1H NMR (d6-DMSO) δ 9.85 (s, 1H), 8.92 (s, 1H), 8.06 (s, 2H), 7.56 (s, 1H), 7.43 (s, 1H), 7.39-7.35 (m, 1H), 7.33-7.29 (m, 1H), 7.20-7.13 (m, 1H), 5.57 (s, 2H), 4.17 (s, 2H), 3.96-3.91 (m, 2H), 3.84 (s, 3H), 3.69-3.64 (m, 2H); LC-MS method B, (ES+) 405.1, RT=6.31 min.

Workup

  1. customthe reaction mixture was partitioned between 0.5M EDTA and DCM
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialthe combined organic phases dried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7674c30a27b64175a3269db93f5f349a
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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