Aluminium lithium hydride → HCID 59128628, compound

HRID 1991013Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

4-Methyl-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-benzoic acid methyl ester (150 mg, 0.422 mmol) was dissolved in 6 mL dry THF. The reaction mixture was cooled to 0° C., and LAH (0.63 mL of 1.0 M solution in THF, 0.633 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 15 minutes, and then the ice bath was removed. Water (0.3 mL) in 2 mL THF was added dropwise. After stirring for 10 minutes, 0.3 mL of 20% aqueous NaOH was added. After stirring for another 10 minutes, 0.8 mL water was added. The reaction mixture was stirred for 90 minutes, then filtered through a Celite pad. The filtrate was concentrated under reduced pressure to give 132 mg of 6-(5-Hydroxymethyl-2-methyl-phenyl)-8-methyl-2-methylsulfanyl-5,8-dihydro-pyrido[2,3-d]pyrimidin-7-ol, MS (M+H)=330.

Workup

customthe ice bath was removed
additionWater (0.3 mL) in 2 mL THF was added dropwise
stirringAfter stirring for 10 minutes
addition0.3 mL of 20% aqueous NaOH was added
stirringAfter stirring for another 10 minutes
addition0.8 mL water was added
stirringThe reaction mixture was stirred for 90 minutes
filtrationfiltered through a Celite pad
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-25939da650ca4a9bb113420cbcf54a0e
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645764B2

Reaction notes

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