Water → (S)-6-(3-Methoxypyrrolidin-1-yl)-2-phenylpyrimidine-4-carboxylic acid

HRID 1896150Notes

Reaction equation

HRID 1896150 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]([OH:16])=[O:15])[CH:3]=1.CC[N:19]([CH:23]([CH3:25])C)[CH:20]([CH3:22])C.[OH2:26].[CH2:27](Cl)Cl>C1COCC1>[CH3:27][O:26][C@H:25]1[CH2:22][CH2:20][N:19]([C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:5]=[C:4]([C:14]([OH:16])=[O:15])[CH:3]=2)[CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 574316986-Chloro-2-phenylpyrimidine-4-carboxylic acid2×

Product 1

HCID 68441504(S)-6-(3-Methoxypyrrolidin-1-yl)-2-phenylpyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

6-chloro-2-phenyl-pyrimidine-4-carboxylic acid (14.3 g; prepared as described in WO 2006/114774, Example 24, intermediate 24.3), intermediate 1.7 (10 g) and DIPEA (23 mL) were dissolved in THF (191 mL). The reaction mixture was stirred at 60° C. for 48 h. Water and DCM were added and the phases were separated. The aq. phases were washed with DCM and the combined org. phases were dried (Na2SO4) and evaporated off. CC (DCM/MeOH 9/1) of the crude yielded the desired compound (13.2 g).

Workup

  1. customthe phases were separated
  2. washThe aq. phases were washed with DCM
  3. dry with materialphases were dried (Na2SO4)
  4. customevaporated off

Sources & evidence

ORD record
ord-baf68312879d4332bc5264c5218fe17c
Source dataset
uspto-grants-2013_08
Patent number
US08518912B2

Reaction notes

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