(S)-3-aminoheptan-1-ol → (S)-2-(4-((2-Amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetonitrile

HRID 2387836Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][CH2:4][OH:5].[NH2:10][C:11]1[N:16]=[C:15](Cl)[C:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C:26]#[N:27])=[CH:21][C:20]=2[F:28])=[C:13]([CH3:29])[N:12]=1>CN1C(=O)CCC1.O>[NH2:10][C:11]1[N:16]=[C:15]([NH:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][CH2:4][OH:5])[C:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C:26]#[N:27])=[CH:21][C:20]=2[F:28])=[C:13]([CH3:29])[N:12]=1

Participants

Conditions

Temperature: 150 °C

Procedure

(S)-3-Aminoheptan-1-ol (0.135 g) was added to a stirred solution of the product from step (iii) (0.12 g) in NMP (2 mL). The mixture was heated at 150° C. for 48 h, and then at 170° C. for a further 8 h. The mixture was allowed to cool, diluted with water (10 mL) and the aqueous extracted with EtOAc. The combined organic phase was dried and evaporated. The crude product was purified by column chromatography, to give the subtitle compound, 0.11 g.

Workup

temperatureto cool
extractionthe aqueous extracted with EtOAc
customThe combined organic phase was dried
customevaporated
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-ea1338bbcde34fa9a2c1eedde734fe03
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268990B2

Reaction notes

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