Methylamine → HCID 66933398, compound

HRID 2069390Notes

Reaction equation

HRID 2069390 reaction equation
[CH3:1][NH2:2].CS([C:7]1[N:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[C:9]([CH2:16][CH2:17][CH3:18])[N:8]=1)(=O)=O>>[CH3:1][NH:2][C:7]1[N:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[C:9]([CH2:16][CH2:17][CH3:18])[N:8]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 54759243HCID 54759243, compound

Product 1

HCID 66933398HCID 66933398, compound

Procedure

A solution of 40% aq. methylamine (5 mL) and 2-methanesulfonyl-6-propyl-pyrimidine-4-carboxylic acid (150 mg, 0.614 mmol) is heated to 70° C. for 2 h. The reaction mixture is then evaporated and the crude compound is dissolved in 3N NaOH solution (10 mL). The aq. solution is washed with EtOAc (5 mL), is then adjusted to pH 3 with 25% aq. HCl and finally extracted with DCM (3×15 mL). The combined DCM extracts are dried over MgSO4, filtered and evaporated to give 2-methylamino-6-propyl-pyrimidine-4-carboxylic acid as a beige powder (128 mg); LC-MS: tR=0.56 min, [M+H]+=196.00.

Workup

  1. customThe reaction mixture is then evaporated
  2. dissolutionthe crude compound is dissolved in 3N NaOH solution (10 mL)
  3. washThe aq. solution is washed with EtOAc (5 mL)
  4. extractionfinally extracted with DCM (3×15 mL)
  5. dry with materialThe combined DCM extracts are dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-788e3448a12141cebeb112661bd30cf1
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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