Aluminium lithium hydride → 4-{5-[5-Methyl-2-(2,2,6,6-tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-thiophen-2-yl}-butan-1-ol

HRID 1434927Notes

Reaction equation

HRID 1434927 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][C:7]1[S:8][C:9]([C:12]2[C:17]([CH3:18])=[CH:16][N:15]=[C:14]([NH:19][CH:20]3[CH2:25][C:24]([CH3:27])([CH3:26])[NH:23][C:22]([CH3:29])([CH3:28])[CH2:21]3)[N:13]=2)=[CH:10][CH:11]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:18][C:17]1[C:12]([C:9]2[S:8][C:7]([CH2:6][CH2:5][CH2:4][CH2:3][OH:2])=[CH:11][CH:10]=2)=[N:13][C:14]([NH:19][CH:20]2[CH2:21][C:22]([CH3:28])([CH3:29])[NH:23][C:24]([CH3:27])([CH3:26])[CH2:25]2)=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 579361484-{5-[5-Methyl-2-(2,2,6,6-tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-thiophen-2-yl}-butyric acid methyl ester

Product 1

HCID 112004814-{5-[5-Methyl-2-(2,2,6,6-tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-thiophen-2-yl}-butan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ester from Step B (37 mg, 0.09 mmol) was dissolved in 1 ml of THF and LAH (1M in THF, 0.22 ml, 0.22 mmol) was added. After 30 minutes, the mixture was quenched with water and extracted with ether. The organic layers were washed with brine, dried over sodium sulfate and evaporated. The crude product was purified by preparative HPLC. Yield: 15 mg (43%).

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted with ether
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-cd8ece670e464abf89f388607553056d
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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