Aluminium lithium hydride → HCID 59614410, compound

HRID 409455Notes

Reaction equation

HRID 409455 reaction equation
C[O:2][C:3]([C:5]1[C:6]([N:17]2[CH2:21][C@@H:20]([N:22]([CH2:35][C:36]3[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[C:38]([C:46]([F:49])([F:48])[F:47])[CH:37]=3)[C:23]3[N:28]=[CH:27][C:26]([C:29]4[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=4)=[CH:25][N:24]=3)[CH2:19][C@H:18]2[CH2:50][CH3:51])=[N:7][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:9][CH:10]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:48][C:46]([F:47])([F:49])[C:38]1[CH:37]=[C:36]([CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=1)[CH2:35][N:22]([C:23]1[N:28]=[CH:27][C:26]([C:29]2[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=2)=[CH:25][N:24]=1)[C@@H:20]1[CH2:21][N:17]([C:6]2[C:5]([CH2:3][OH:2])=[CH:10][N:9]=[C:8]([N:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[N:7]=2)[C@H:18]([CH2:50][CH3:51])[CH2:19]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59614359HCID 59614359, compound

Product 1

HCID 59614410HCID 59614410, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-2-piperidin-1-yl-pyrimidine-5-carboxylic acid methyl ester (250 mg, 0.33 mmol) in 1.5 mL of THF is added LAH (24 mg, 0.66 mmol). After stirred at room temperature for 3.5 hours, the reaction is quenched by Glauber's salt. The mixture is filtered on celite, and the filtrate is concentrated. The obtained residue is purified by silica gel column chromatography (eluent: hexane/EtOAc) to give [4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-2-piperidin-1-yl-pyrimidin-5-yl]-methanol (40 mg, 20% yields); ESI-MS m/z: 690 [M+1]+, Retention time 5.79 min (condition B).

Workup

  1. customthe reaction is quenched by Glauber's salt
  2. filtrationThe mixture is filtered on celite
  3. concentrationthe filtrate is concentrated
  4. customThe obtained residue is purified by silica gel column chromatography (eluent: hexane/EtOAc)

Sources & evidence

ORD record
ord-c704939dcca04982be8c855f3ff912cc
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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