Water → HCID 71236584, compound

HRID 2280736Notes

Reaction equation

HRID 2280736 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.Cl.[NH2:13][C@@H:14]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]([OH:21])[CH2:15]1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[OH:21][C@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20][C@@H:14]([NH:13][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=2)[CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 86676338HCID 86676338, compound

Product 1

HCID 71236584HCID 71236584, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring solution of 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (0.4 g, 2.155 mmol) and (1S,3R)-3-aminocycloheptanol hydrochloride (0.428 g, 2.59 mmol; synthesis described herein) in DMF (3 mL) was added DIEA (1.126 mL, 6.46 mmol) and stirred at 60° C. for 1 h. LCMS shows the reaction to be completed. The reaction mixture was cooled to room temperature, and poured into water (50 mL). The suspension was stirred for five minutes, then filtered to afford 4-((1R,3S)-3-hydroxycycloheptylamino)-2-(methylthio)pyrimidine-5-carbonitrile (0.404 g, 1.451 mmol, 67.4% yield) as an off-white solid; 1H NMR (DMSO-d6, 400 MHz): δ ppm 8.39 (s, 1H), 8.00 (d, J=7.4 Hz, 1H), 4.63 (d, J=3.9 Hz, 1H), 4.21 (br. s., 1H), 3.74 (td, J=8.5, 4.1 Hz, 1H), 2.47 (s, 3H), 1.66-1.97 (m, 5H), 1.35-1.66 ppm (m, 5H); MS (ESI) m/z 138.1 [M+1]+.

Workup

  1. customsynthesis
  2. customthe reaction
  3. temperatureThe reaction mixture was cooled to room temperature
  4. stirringThe suspension was stirred for five minutes
  5. filtrationfiltered

Sources & evidence

ORD record
ord-0cf8876f82b54fc6bfba59d151c9545c
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

Loading…