Water → HCID 59446992, compound

HRID 1946677Notes

Reaction equation

HRID 1946677 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[N:3]=1.[CH:13]1([CH2:16][NH:17][CH2:18][CH2:19][CH3:20])[CH2:15][CH2:14]1.C(N(CC)CC)C.O>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=[C:6]([N:17]([CH2:16][CH:13]2[CH2:15][CH2:14]2)[CH2:18][CH2:19][CH3:20])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 117787Cyclopropanemethanamine, N-propyl-HCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylate

Product 1

HCID 59446992HCID 59446992, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled (0° C.) solution of methyl 2,4-dichloropyrimidine-6-carboxylate (Apollo, 10.00 g; 48.3 mmol) in dry THF (200 ml) was treated dropwise over 1 hour with a solution of N-(cyclopropylmethyl)propane-1-amine (6.92 ml; 48.3 mmol) and triethylamine (7.37 ml; 53.1 mmol) in THF (100 ml). The reaction mixture was stirred at room temperature for 18 hours. Water (200 mL) was poured into the reaction mixture, which was extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and concentrated under vacuum to afford the crude product, which was precipitated from MTBE (50 mL) to give the title compound as a beige solid.

Workup

  1. extractionwas extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto afford the crude product, which
  6. customwas precipitated from MTBE (50 mL)

Sources & evidence

ORD record
ord-8ebd49ee0eb14888a037ff58f2242899
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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