Methanol → HCID 59380147, compound

HRID 2353688Notes

Reaction equation

HRID 2353688 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([OH:16])=[O:15])[CH:11]=[C:10]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][C@@H:18]3[CH3:23])[N:9]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:29]O>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([O:16][CH3:29])=[O:15])[CH:11]=[C:10]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][C@@H:18]3[CH3:23])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 59380047HCID 59380047, compound

Product 1

HCID 59380147HCID 59380147, compound

Conditions

Temperature
80 °C

Procedure

2-(4-Aminophenyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine-4-carboxylic acid (1.15 g) was dissolved in methanol (15 mL), sulfuric acid (0.01 mL) was added and the reaction was heated at 80° C. for 24 h. A small quantity of activated molecular sieve 4A was added to the reaction and stirred for 2 h. The reaction was filtered, vacuumed to dryness then suspended in ethyl acetate (250 mL) and washed once with a saturated solution of sodium bicarbonate (250 mL). The organic layer was filtered, dried over magnesium sulphate and vacuumed to dryness to give the desired material as a brown solid (405 mg).

Workup

  1. filtrationThe reaction was filtered
  2. washwashed once with a saturated solution of sodium bicarbonate (250 mL)
  3. filtrationThe organic layer was filtered
  4. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-2445111578534c1c844129130ffe2134
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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