Dichloromethane → HCID 57699761, compound

HRID 1010962Notes

Reaction equation

HRID 1010962 reaction equation
[CH3:1][CH:2]([CH2:21][CH3:22])[CH2:3][O:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[C:7]([NH2:20])[N:6]=1.C1C(=O)N([Br:30])C(=O)C1.C(Cl)Cl>C(Cl)(Cl)Cl>[Br:30][C:10]1[N:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[C:12]2[C:8]([N:9]=1)=[C:7]([NH2:20])[N:6]=[C:5]([O:4][CH2:3][CH:2]([CH3:1])[CH2:21][CH3:22])[N:13]=2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 57699796HCID 57699796, compound

Product 1

HCID 57699761HCID 57699761, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-[(2-methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (245 mg) in dry chloroform (2.9 mL) was cooled to 0° C. and NBS (150 mg) was added to give a green/brown solution. The reaction mixture was stirred at room temperature for 6 h. The mixture was taken up into DCM (20 mL) and was washed with water (20 mL). The organics were separated, dried by passing through a hydrophobic frit and concentrated in vacuo to give the title compound as green solid (292 mg).

Workup

  1. customto give a green/brown solution
  2. washwas washed with water (20 mL)
  3. customThe organics were separated
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-712e640cfca241a48890d11d16a96b70
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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