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

HRID 1617179Notes

Reaction equation

HRID 1617179 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. 1H NMR (DMSO-d6); δ 7.11 (d, 1H), 7.04 (d, 1H), 6.89 (s, 1H), 6.84 (dd, 2H), 5.27 (t, 1H), 4.46 (d, 2H), 3.92 (s, 2H), 2.21 (s, 3H)

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-0b2ce8d06a294451b98533bd80a000d7
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

Loading…