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Water → 2-chloro-4-[(R)-2-(naphthalen-1-yloxymethyl)pyrrolidin-1-yl]pyrimidine

HRID 1036166
Notes
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Reaction equation

HRID 1036166 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(N(C(C)C)C(C)C)C.[C:18]1([O:28][CH2:29][C@H:30]2[CH2:34][CH2:33][CH2:32][NH:31]2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.O>C(O)(C)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:31]2[CH2:32][CH2:33][CH2:34][C@@H:30]2[CH2:29][O:28][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[CH:5]=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 46845432(R)-2-(naphthalen-1-yloxymethyl)pyrrolidine

Product 1

HCID 497661942-chloro-4-[(R)-2-(naphthalen-1-yloxymethyl)pyrrolidin-1-yl]pyrimidineYield 64.4%

Reagents, catalysts & solvents 2

HCID 3776
Isopropanol
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

327 mg of 2,4-dichloropyrimidine are dissolved in 20 ml of isopropanol, and 0.8 ml of N-ethyldiisopropylamine and 500 mg of (R)-2-(naphthalen-1-yloxymethyl)pyrrolidine are added. This mixture is warmed at 80° C. for 6 h. After cooling, the batch is poured into 40 ml of water and 40 ml of ethyl acetate. After phase separation, the organic phase is dried, evaporated and chromatographed on silica gel, giving 480 mg of 2-chloro-4-[(R)-2-(naphthalen-1-yloxymethyl)pyrrolidin-1-yl]pyrimidine as colourless oil;

Workup

  1. temperatureAfter cooling
  2. customAfter phase separation
  3. customthe organic phase is dried
  4. customevaporated
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-9e861771b4794dd2a7630687df19aba4
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546406B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes