Sodium Sulfate → 6-[4-(4-Ethyl-piperazin-1-ylmethyl)-phenyl]-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-7H-pyrrolo[2,3-d]pyrimidine

HRID 133052Notes

Reaction equation

HRID 133052 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[NH:47][C:30]4[N:31]=[CH:32][N:33]=[C:34]([O:35][C:36]5[C:37]([F:46])=[C:38]6[C:42](=[CH:43][CH:44]=5)[NH:41][C:40]([CH3:45])=[CH:39]6)[C:29]=4[CH:28]=3)=[CH:23][CH:22]=2)=O)[CH2:15][CH2:14]1)[CH3:12].[NH4+].[Cl-].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O.CCOC(C)=O>[CH2:11]([N:13]1[CH2:14][CH2:15][N:16]([CH2:19][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[NH:47][C:30]4[N:31]=[CH:32][N:33]=[C:34]([O:35][C:36]5[C:37]([F:46])=[C:38]6[C:42](=[CH:43][CH:44]=5)[NH:41][C:40]([CH3:45])=[CH:39]6)[C:29]=4[CH:28]=3)=[CH:23][CH:22]=2)[CH2:17][CH2:18]1)[CH3:12]

Participants

8

Reactant 4

HCID 24436Sodium SulfateHCID 25517Ammonium ChlorideHCID 10207082(4-Ethyl-piperazin-1-yl]-[4-[4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl]-methanoneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 102063036-[4-(4-Ethyl-piperazin-1-ylmethyl)-phenyl]-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.56 ml of diisobutyl-aluminium hydride (1 M in THF) are added to a solution of 130 mg (0.26 mMol) of (4-ethyl-piperazin-1-yl)-{4-[4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}methanone in 13 ml of THF at −15° C. under a N2-atmosphere. After 3 h, 4 ml of EtOAc are added to the solution, followed by 0.2 ml of a saturated solution of NH4Cl in water. After adding solid Na2SO4, the reaction mixture is filtered through Celite. The filtrate is concentrated together with 3 g of SiO2. The resulting powder is put on top of a chromatography column (SiO2) and then eluted with EtOAc/methanol 4:1 and finally EtOAc/methanol/NEt3 80:20:1, yielding the title compound; HPLC (conditions see Examples 67-78) tR=10.5 min; MS-ES+: (M+H)+=485.

Workup

  1. filtrationthe reaction mixture is filtered through Celite
  2. concentrationThe filtrate is concentrated together with 3 g of SiO2
  3. washeluted with EtOAc/methanol 4:1 and finally EtOAc/methanol/NEt3 80:20:1

Sources & evidence

ORD record
ord-13a3336e54304af2b23adb1973377f47
Source dataset
uspto-grants-2008_06
Patent number
US07390805B2

Reaction notes

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