Dichloromethane → HCID 59380152, compound

HRID 2353634Notes

Reaction equation

HRID 2353634 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C@@H:10]2[CH3:15])[N:6]=[C:5]([C:16]2[CH:21]=[CH:20][C:19]([NH:22]C(=O)OC(C)(C)C)=[CH:18][CH:17]=2)[N:4]=1.C(Cl)Cl>Cl.O1CCOCC1>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:5]2[N:4]=[C:3]([CH2:2][OH:1])[CH:8]=[C:7]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][C@@H:10]3[CH3:15])[N:6]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 59379892HCID 59379892, compound

Product 1

HCID 59380152HCID 59380152, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl N-[4-[4-(hydroxymethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]carbamate (1.20 g) was dissolved in 4M hydrogen chloride in dioxane (5 mL) and dioxane (5 mL). The reaction was stirred for 18 hour then DCM (10 mL) added to help solubilise material. The reaction was stirred at 40° C. for a further 18 hours then evaporated to dryness. The solid was suspended in DCM (20 mL) and a mixture of a saturated aqueous solution of sodium hydrogen carbonate (6 mL) and water (4 mL) was added. The organics were separated, dried (MgSO4) and concentrated in vacuo to give the desired compound (648 mg) as a pale yellow solid.

Workup

  1. stirringThe reaction was stirred at 40° C. for a further 18 hours
  2. customthen evaporated to dryness
  3. additiona mixture of a saturated aqueous solution of sodium hydrogen carbonate (6 mL) and water (4 mL)
  4. additionwas added
  5. customThe organics were separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24dd4706a4934d2e91a1e01458f7838a
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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