Diisopropylethylamine → (5S)-5-[(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)amino]-1-methyl-2-piperidinone

HRID 1751792Notes

Reaction equation

HRID 1751792 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.C(N(C(C)C)CC)(C)C.[NH2:21][C@@H:22]1[CH2:27][N:26]([CH3:28])[C:25](=[O:29])[CH2:24][CH2:23]1>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C@@H:22]2[CH2:27][N:26]([CH3:28])[C:25](=[O:29])[CH2:24][CH2:23]2)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 28064098HCID 28064098, compoundHCID 457899672,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine

Product 1

HCID 59708467(5S)-5-[(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)amino]-1-methyl-2-piperidinone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

0.27 g (II) are placed in 3 ml dioxane, then first 0.45 ml diisopropylethylamine are added, followed by 0.25 g (S)-5-amino-1-methylpiperidin-2-one. The reaction mixture is heated to 130° C. until there is no further reaction then cooled and evaporated down. The product is extracted with dichloromethane and purified by chromatography (preparative HPLC, method A). 0.26 g (III-5) are obtained in the form of a solid. Analytical HPLC-MS (method A): RT=1.06 min.

Workup

  1. customno further reaction
  2. temperaturethen cooled
  3. customevaporated down
  4. extractionThe product is extracted with dichloromethane
  5. custompurified by chromatography (preparative HPLC, method A)
  6. custom0.26 g (III-5) are obtained in the form of a solid

Sources & evidence

ORD record
ord-4fdd543004ca4762b4f12193b011c4b3
Source dataset
uspto-grants-2015_10
Patent number
US09161927B2

Reaction notes

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