Dichloromethane → HCID 57816841, compound

HRID 2197460Notes

Reaction equation

HRID 2197460 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:7]1=[N:8][C:9]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[N:10][C:11]=2[NH2:15].[CH2:24]([O:26][P:27]([O-:31])[O:28][CH2:29][CH3:30])[CH3:25].C(N(CC)CC)C.C(Cl)Cl>CN(C=O)C.C(OCC)(=O)C>[NH2:15][C:11]1[N:10]=[C:9]([O:16][CH2:17][CH2:18][O:19][CH3:20])[N:8]=[C:7]2[C:12]=1[N:13]=[CH:14][N:6]2[CH2:5][C:4]1[CH:3]=[C:2]([P:27](=[O:31])([O:28][CH2:29][CH3:30])[O:26][CH2:24][CH3:25])[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 57816858HCID 57816858, compound

Product 1

HCID 57816841HCID 57816841, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

9-(3-bromobenzyl)-2-(2-methoxyethoxy)-9H-purin-6-amine (29) (500 mg, 1.32 mmol) was suspended in DMF (5 mL). Diethylphosphite (0.26 mL, 2.0 mmol), triethylamine (0.28 mL, 2.0 mmol) and (1,1′-Bis(diphenylphosphino)ferrocene)dichloropalladium(II), complex with CH2Cl2 (106 mg, 0.13 mmol) was added and the mixture was heated at 130° C. for 5 min in a microwave reactor. Then the reaction mixture was diluted with ethyl acetate (150 mL) and washed with water and brine. The organic solution was dried with sodium sulfate and the solvent was removed under vacuum. The residue was redissolved in ethyl acetate (10 mL) and adsorbed on a short column of silica gel. The product was eluted with dichloromethane/methanol 1:0 to 1:1 giving diethyl 3-((6-amino-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenylphosphonate (30) (400 mg, 70%) as a dark brown oil after evaporation of the solvent. MS: 436 (MH+).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic solution was dried with sodium sulfate
  3. customthe solvent was removed under vacuum
  4. dissolutionThe residue was redissolved in ethyl acetate (10 mL)
  5. washThe product was eluted with dichloromethane/methanol 1:0 to 1:1 giving diethyl 3-((6-amino-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenylphosphonate (30) (400 mg, 70%) as a dark brown oil
  6. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-bcd0670d50284dba8a4e5c459f747145
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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