Aluminium lithium hydride → AZD 8055

HRID 218353Notes

Reaction equation

HRID 218353 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C@H:8]1[CH2:13][O:12][CH2:11][CH2:10][N:9]1[C:14]1[N:15]=[C:16]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][C@@H:37]2[CH3:42])[C:17]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[CH:26][C:27]([O:34][CH3:35])=[C:28]([CH:33]=3)[C:29](OC)=[O:30])=[N:20][C:18]=2[N:19]=1>C1COCC1>[CH3:7][C@H:8]1[CH2:13][O:12][CH2:11][CH2:10][N:9]1[C:14]1[N:15]=[C:16]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][C@@H:37]2[CH3:42])[C:17]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[CH:26][C:27]([O:34][CH3:35])=[C:28]([CH2:29][OH:30])[CH:33]=3)=[N:20][C:18]=2[N:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 59703378HCID 59703378, compound

Product 1

HCID 25262965AZD 8055Yield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminium hydride (2M solution in THF, 1.01 mL, 2.01 mmol) was added to a solution of methyl 5-{2,4-bis[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d]pyrimidin-7-yl}-2-methoxybenzoate (1.47 g, 2.68 mmol) in THF (19.8 mL) at 0° C. under an atmosphere of nitrogen. After 60 minutes, further lithium aluminium hydride (2M solution in THF, 0.67 mL, 1.34 mmol) was added and the solution allowed to stir at RT for 900 minutes. The resulting solution was quenched by the addition of water (11.76 mL) and extracted with ethyl acetate (22 mL). On evaporation of the ethyl acetate, 1.2 g of (5-{2,4-bis[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d]pyrimidin-7-yl}-2-methoxyphenyl)methanol (6) is obtained as a yellow solid.

Workup

  1. customThe resulting solution was quenched by the addition of water (11.76 mL)
  2. extractionextracted with ethyl acetate (22 mL)
  3. customOn evaporation of the ethyl acetate

Sources & evidence

ORD record
ord-5801a18097ec4e94b2964a4223ec5a7d
Source dataset
uspto-grants-2012_06
Patent number
US08198441B2

Reaction notes

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