Diisopropylethylamine → HCID 86671787, compound

HRID 1410116Notes

Reaction equation

HRID 1410116 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=1.[Cl:14][C:15]1[N:16]=[C:17](Cl)[C:18]2[N:23]=[CH:22][S:21][C:19]=2[N:20]=1.CCN(C(C)C)C(C)C>CC(O)C>[Cl:14][C:15]1[N:16]=[C:17]([NH:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([N:3]3[CH2:4][CH2:5][CH2:6][C@@H:2]3[CH3:1])[CH:8]=2)[C:18]2[N:23]=[CH:22][S:21][C:19]=2[N:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6096395,7-Dichlorothiazolo(5,4-d)pyrimidineHCID 68379149HCID 68379149, compound

Product 1

HCID 86671787HCID 86671787, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of (S)-3-(2-methylpyrrolidin-1-yl)benzenamine (0.9 g, 5.34 mmol), 5,7-dichlorothiazolo[5,4-d]pyrimidine (1.1 g, 5.34 mmol), DIEA (1.4 g, 10.68 mmol) in IPA (15 mL) was heated to reflux for 2 hours. Then the reaction mixture was concentrated and residue purified by column chromatography (petroleum ether:ethyl acetate=8:1) to give (S)-5-chloro-N-(3-(2-methylpyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (1.6 g, 91.4%) as yellow solid. LC-MS: 346 [M+H]+, tR=1.82 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. concentrationThen the reaction mixture was concentrated
  4. customresidue purified by column chromatography (petroleum ether:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-b00fce37267344428de10abc55af989a
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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