Carbon tetrabromide → HCID 68531693, compound

HRID 2099231Notes

Reaction equation

HRID 2099231 reaction equation
[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:21]=[N:20][C:19]4[C:14]3=[N:15][CH:16]=[N:17][C:18]=4[C:22]3[CH:27]=[CH:26][C:25]([CH2:28]O)=[CH:24][CH:23]=3)[CH:7]=2)[CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:32][CH2:28][C:25]1[CH:26]=[CH:27][C:22]([C:18]2[N:17]=[CH:16][N:15]=[C:14]3[C:19]=2[N:20]=[CH:21][N:13]3[C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=2[CH3:12])[C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:30])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11618227HCID 11618227, compound

Product 1

HCID 68531693HCID 68531693, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-cyclopropyl-3-[6-(4-hydroxymethyl-phenyl)-purin-9-yl]-4-methyl-benzamide (58 mg, 0.145 mmol, see example 4C-3 1) in dichloromethane (0.5 ml) was added carbon tetrabromide (58 mg, 0.175 mmol) then triphenylphosphine (47 mg, 0.179 mmol). The mixture was stirred at RT for an hour, then purified by a column eluting with EtOAc/Hex. (1:1) to give the desired product as a crude (88 mg, 0.19 mmol, 63%).

Workup

  1. custompurified by a column
  2. washeluting with EtOAc/Hex

Sources & evidence

ORD record
ord-cb1875f5c1bf44babfc2031edf118fc9
Source dataset
uspto-grants-2009_08
Patent number
US07569571B2

Reaction notes

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