Isopropylamine → HCID 10491237, compound

HRID 2280774Notes

Reaction equation

HRID 2280774 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.CC[N:17](C(C)C)[CH:18]([CH3:20])[CH3:19].C(N)(C)C>>[CH:18]([NH:17][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1)([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 6363Isopropylamine2×HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 10491237HCID 10491237, compoundYield 105.4%

Procedure

Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (900 g, 3.87 mol) ethanol (12 L), DIEA (876 mL, 5.05 mol), and isopropylamine (379 mL, 4.45 mol) were combined and mixed at ambient temperature for 4 h. An additional amount of isopropylamine (50 mL, 0.59 mol) was added and the mixture was stirred overnight at ambient temperature. The reaction was concentrated under reduced pressure and the crude product was diluted with water (2 L). The aqueous layer was extracted with chloroform (2×3 L). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford ethyl 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylate (1042 g, 4.08 mol, >100% yield, contaminated with trace DIEA) as a pale brown oil that was used without further purification. MS (ESI) m/z 256.4 [M+1]+.

Workup

  1. additionmixed at ambient temperature for 4 h
  2. concentrationThe reaction was concentrated under reduced pressure
  3. additionthe crude product was diluted with water (2 L)
  4. extractionThe aqueous layer was extracted with chloroform (2×3 L)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-789d72013a7c4ccfbb3a0908c18d8ab6
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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