Water → HCID 57910757, compound

HRID 1644860Notes

Reaction equation

HRID 1644860 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C:8]1[N:13]=[CH:12][CH:11]=[CH:10][N:9]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][C:8]1[N:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27630242-Pyrimidinemethanol

Product 1

HCID 57910757HCID 57910757, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (4.40 mL, 57.1 mmol) was added to a stirred solution of 2-hydroxymethylpyrimidine (6.28 g, 57.1 mmol) and triethylamine (9.50 mL, 68.5 mmol) in DCM (250 mL) at 0° C. After approximately 20 min, the reaction mixture was poured into water, the organic layer was separated and the aqueous phase was re-extracted twice with DCM. The combined organic extracts were washed with water, brine, dried (sodium sulfate), and concentrated in vacuo to afford the title compound i-2a. 1HNMR (500 MHz, CDCl3): δ 8.81 (d, 2H, J=4.8 Hz), 7.32 (t, 1H, J=4.9 Hz), 5.46 (s, 2H), 3.24 (s, 3H).

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous phase was re-extracted twice with DCM
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16e2e21f59f44f26a0c93d3630e83772
Source dataset
uspto-grants-2012_02
Patent number
US08124628B2

Reaction notes

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