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

HRID 2387833Notes

Reaction equation

HRID 2387833 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[F:30])=[C:14]([CH3:31])[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[F:30])=[C:14]([CH3:31])[N:13]=1

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86633399Methyl 4-((2-amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-fluorobenzoate

Product 1

HCID 86633403(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of diisobutylaluminium hydride (1M in hexanes, 8.8 mL) was added dropwise over 10 min to a suspension of the product from example 22 step (iii) (0.78 g) in THF (10 mL) at 0° C. The mixture was allowed to warm to rt and stirred for 1 h. EtOAc (10 mL) was added and then the mixture stirred for 10 min before being 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, 0.3 g.

Workup

  1. stirringthe mixture stirred for 10 min
  2. stirringThe mixture was stirred for 30 min
  3. customThe organic phase was separated
  4. extractionthe aqueous was extracted with EtOAc
  5. customThe combined organic phase was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9b2ea98ae14b4bf1b150679137275b36
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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