Methanol → HCID 86633857, compound

HRID 1040696Notes

Reaction equation

HRID 1040696 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([NH2:9])=[O:8].CO.[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([Cl:20])=[CH:15][N:14]=1.C(=O)(O)[O-].[Na+]>O>[Cl:12][C:13]1[N:18]=[C:17]([NH:1][C@H:2]2[CH2:6][CH2:5][CH2:4][C@H:3]2[C:7]([NH2:9])=[O:8])[C:16]([Cl:20])=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 2372592,4,5-TrichloropyrimidineHCID 516892Sodium BicarbonateHCID 2733686HCID 2733686, compound

Product 1

HCID 86633857HCID 86633857, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred solution of cis-2-amino-cyclopentanecarboxylic acid amide (1 g, 0.008 mol) in methanol (20 mL, 0.5 mol) and water (10 mL, 0.6 mol) at 0° C. in an ice bath was added 2,4,5-trichloropyrimidine (1.7 g, 0.0094 mol) followed by sodium bicarbonate (1 g, 0.02 mol). The reaction mixture was warmed to room and stirred at room temperature for 24 h. The reaction mixture was diluted with water (25 mL) and washed with ethyl acetate (3×50 mL). The organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to give cis-2-(2,5-dichloro-pyrimidin-4-ylamino)-cyclopentanecarboxylic acid amide as a white solid (1.8 g, 80% yield). No further purification was needed. 1HNMR (400 MHz, CDCl3) δ 7.99 (s, 1H), 6.73 (d, 1H, J=6.8 Hz), 5.56 (broad s, 1H), 5.44 (broad s, 1H), 4.66 (p, 1H, J=7.5 Hz), 2.97 (q, 1H, J=7.5 Hz), 2.05-2.15 (m, 3H), 1.83-1.98 (m, 2H), 1.70 (m, 1H).

Workup

  1. temperatureThe reaction mixture was warmed to room
  2. washwashed with ethyl acetate (3×50 mL)
  3. dry with materialThe organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae9a5389c6fb4e8f8779f20ac7caa499
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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