1-Butanol → (s)-2-(4-((2-Amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)phenyl)acetic acid

HRID 1617252

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][C:10]2[CH:15]=[CH:14]C(CC#N)=C[CH:11]=2)=[C:4]([CH3:19])[N:3]=1.[NH2:20][C@@H:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][OH:24].[OH-:28].[K+].[CH2:30]([OH:34])[CH2:31][CH2:32][CH3:33]>>[NH2:1][C:2]1[N:7]=[C:6]([NH:20][C@@H:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][OH:24])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:32]([CH2:31][C:30]([OH:28])=[O:34])=[CH:33][CH:11]=2)=[C:4]([CH3:19])[N:3]=1

Participants

Reactant 4

HCID 2631-Butanol

HCID 14797Potassium Hydroxide

HCID 11062353(S)-3-aminohexan-1-ol

HCID 874447822-(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)phenyl)acetonitrile

Product 1

HCID 68957300(s)-2-(4-((2-Amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)phenyl)acetic acid

Conditions

Temperature: 100 °C

Procedure

A mixture of the product of example 81 step (iii) (0.4 g) and (S)-3-aminohexan-1-ol (0.5 g) in butan-1-ol (3 mL) was sealed into a microwave tube. The reaction was performed in the CEM Microwave, at 160° C. and 100 W for 1.5 h. Aq. 5M KOH (iml) was added and the mixture heated at 100° C. for 48 h. The mixture was cooled and the solvent evaporated under reduced pressure. The residue was purified by RPHPLC to give the subtitle compound, 174 mg.

Workup

customwas sealed into a microwave tube
customwas performed in the CEM Microwave, at 160° C.
temperatureThe mixture was cooled
customthe solvent evaporated under reduced pressure
customThe residue was purified by RPHPLC

Sources & evidence

ORD record: ord-9d98d595517e4862b82eace92a89943c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765939B2

Linked notes

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