Diisobutylaluminumhydride → (4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)methanol

HRID 1617171Notes

Reaction equation

HRID 1617171 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[NH2:11][C:12]1[N:17]=[C:16]([Cl:18])[C:15]([CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24](OC)=[O:25])=[CH:22][C:21]=2[O:30][CH3:31])=[C:14]([CH3:32])[N:13]=1>C1COCC1.CCOC(C)=O>[NH2:11][C:12]1[N:17]=[C:16]([Cl:18])[C:15]([CH2:19][C:20]2[CH:29]=[CH:28][C:23]([CH2:24][OH:25])=[CH:22][C:21]=2[O:30][CH3:31])=[C:14]([CH3:32])[N:13]=1

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86633398Methyl 4-((2-amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzoate

Product 1

HCID 86633400(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of diisobutylaluminium hydride (1M in hexanes, 5.44 mL) was added over 10 min to a suspension of the product from example 21 step (iii) (0.5 g) in THF (10 mL) at 0° C. The mixture was allowed to warm to rt and stirred for Ih. EtOAc (10 mL) was added cautiously and then the reaction mixture was added to ice/water (100 mL). The mixture was stirred for 30 min and then diluted with EtOAc (50 mL). The organic phase was separated and the aqueous was extracted with EtOAc. The combined organic phase was dried, filtered and evaporated to afford the subtitle compound, 0.39 g.

Workup

  1. stirringThe mixture was stirred for 30 min
  2. customThe organic phase was separated
  3. extractionthe aqueous was extracted with EtOAc
  4. customThe combined organic phase was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-494a29e026174bac9a49de65f569bb44
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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