Dichloromethane → 8-Bromo-2-[(2,2-dimethylpentyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1010947Notes

Reaction equation

HRID 1010947 reaction equation
[CH3:1][C:2]([CH3:24])([CH2:21][CH2:22][CH3:23])[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:32])C(=O)C1.C(Cl)Cl>C(Cl)(Cl)Cl>[Br:32][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][C:2]([CH3:24])([CH3:1])[CH2:21][CH2:22][CH3:23])[N:13]=2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 576997982-[(2,2-Dimethylpentyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 576997978-Bromo-2-[(2,2-dimethylpentyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amineYield 103.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2-[(2,2-dimethylpentyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (372 mg) in dry chloroform (4.05 mL) at 0° C. was added NBS (209 mg) in a single portion. The reaction was warmed to room temperature and was stirred for 5 h. The mixture was taken up into DCM (20 mL) and washed with water (30 mL). The organics were separated and dried using a hydrophobic frit then concentrated in vacuo to afford the title compound as a green/brown viscous foam (475 mg).

Workup

  1. washwashed with water (30 mL)
  2. customThe organics were separated
  3. customdried
  4. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-672c12ae6d83471e83a0332c73990885
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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