Carbon tetrabromide → HCID 59834599, compound

HRID 271595Notes

Reaction equation

HRID 271595 reaction equation
[CH:1]1([N:7]2[C:11]3[N:12]=[C:13]([C:16]#[N:17])[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:47]>C(Cl)Cl>[Br:47][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][C:8]2[N:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:11]3[N:12]=[C:13]([C:16]#[N:17])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 59834732HCID 59834732, compound

Product 1

HCID 59834599HCID 59834599, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-cyclohexyl-6-(4-hydroxymethyl-benzyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.43 mmol) in CH2Cl2 (5 ml), triphenylphosphine (0.47 mmol) and carbontetrabromide (0.47 mmol) are added at 0° C. under nitrogen. The reaction mixture is stirred at 0° C. for 1 h and at room temperature for 1 h. The crude product is applied to a column of silica gel, which is eluted with following solvents: n-hexane:AcOEt=10:1 (v/v), n-hexane:AcOEt=8:1 (v/v) and n-hexane:AcOEt=5:1 (v/v). The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford the title compound. yield 73.9%, Rf=0.72 (n-hexane:AcOEt=1:1).

Workup

  1. washis eluted with following solvents
  2. customThe solvent of the latter effluent is removed by evaporation
  3. customdried in vacuo

Sources & evidence

ORD record
ord-d11154419442446eb92f5bb45ebdcbfc
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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