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Potassium Carbonate → HCID 86633877, compound

HRID 1687121
Notes
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Reaction equation

HRID 1687121 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[OH:9].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([Cl:24])=[CH:19][N:18]=1>O1CCCC1>[Cl:16][C:17]1[N:22]=[C:21]([NH:2][C@@H:3]2[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]2[OH:9])[C:20]([Cl:24])=[CH:19][N:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

Product 1

HCID 86633877HCID 86633877, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (100 mL) was added to racemic trans-2-amino-cyclohexanol hydrochloride (4.28 g, 28.2 mmol) and potassium carbonate (12.1 g, 88 mmol). The mixture was cooled at 0° C. before 2,4,5-trichloropyrimidine (2 mL, 17.4 mmol) was added. After 3 hours, the mixture was partitioned between water and ethyl acetate, the aq. layer was extracted and the combined extracts were dried and conc. in vacuo. The crude product was taken up in ethyl acetate and washed with 10% w/v citric acid, then with sodium bicarbonate, dried over sodium sulfate and conc. in vacuo to give rel-(1R,2R)-2-(2,5-dichloro-pyrimidin-4-ylamino)-cyclohexanol (2.27 g, 50%) as a white solid. m.p.=139-142° C.; LCMS (m/e) 262 (M+1); 1H-NMR (DMSO-d6, 400 MHz) δ 8.12 (s, 1H), 7.45 (m, 1H), 68 (m, 1H), 3.81 (m, 1H), 3.55 (m, 1H), 1.92 (m, 1H), 1.81 (m, 1H), 1.67 (m, 2H), 1.41 (m, 1H), 1.26 (m, 3H).

Workup

  1. additionwas added
  2. customthe mixture was partitioned between water and ethyl acetate
  3. extractionthe aq. layer was extracted
  4. customthe combined extracts were dried and conc. in vacuo
  5. washwashed with 10% w/v citric acid
  6. dry with materialwith sodium bicarbonate, dried over sodium sulfate and conc. in vacuo

Sources & evidence

ORD record
ord-3eafe032239b4631a56031c688e3e1a6
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148391B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes