Water → HCID 178519399, compound

HRID 1946998Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[C:12]2[CH:13]=[CH:14][N:15]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH:27]4[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]4)[N:21]=3)[C:16]=2[CH:17]=[CH:18][CH:19]=1)=O.O.[OH-].[Na+]>C1COCC1>[OH:8][CH2:9][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][N:15]2[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C@H:27]2[CH2:32][CH2:31][C@H:30]([OH:33])[CH2:29][CH2:28]2)[N:21]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of LAH (1 M in THF, 0.57 mL) was slowly added at −10° C. under argon atmosphere to a solution of 1-[2-(4-hydroxycyclohexylamino)-pyrimidin-4-yl]-1H-indole-4-carboxylic acid methyl ester (100 mg) in THF (0.3 mL). The resulting mixture was stirred at −10° C. for 30 min, and at RT overnight. The reaction mixture was then cooled to 0° C. and water (20 μL) was added, followed by aqueous NaOH (15%, 20 μL) and a second aliquot of water (70 μL). The resulting mixture was stirred for 30 min, then filtered through a CELITE™ pad. The inorganic salts were triturated, the supernatant added to the filtrate, and the solution evaporated under reduced pressure to give trans-4-[4-(4-hydroxymethylindol-1-yl)-pyrimidin-2-ylamino]-cyclohexanol (32.5 g, 35% yield) as a white solid. MS=339 [M+H]+; MP=212.0-213.3° C.

Workup

customat RT
customovernight
temperatureThe reaction mixture was then cooled to 0° C.
stirringThe resulting mixture was stirred for 30 min
filtrationfiltered through a CELITE™ pad
customThe inorganic salts were triturated
additionthe supernatant added to the filtrate
customthe solution evaporated under reduced pressure

Sources & evidence

ORD record: ord-5e4be128dc0742ba82e5c8401f60e318
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399462B2

Reaction notes

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