Ammonia → HCID 178508629, compound

HRID 1163185Notes

Reaction equation

HRID 1163185 reaction equation
[NH3:1].Cl[C:3]1[C:4]2[C:11]([I:12])=[CH:10][N:9]([C@H:13]3[CH2:16][C@H:15]([CH2:17][OH:18])[CH2:14]3)[C:5]=2[N:6]=[CH:7][N:8]=1.C(=O)=O.CC(C)=O>O1CCOCC1.CC(O)C>[NH2:1][C:3]1[C:4]2[C:11]([I:12])=[CH:10][N:9]([C@H:13]3[CH2:16][C@H:15]([CH2:17][OH:18])[CH2:14]3)[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 18522661Acetone cardiceHCID 178521038HCID 178521038, compound

Product 1

HCID 178508629HCID 178508629, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Gaseous ammonia (from a lecture bottle) was condensed into a suspension of trans-[3-(4-chloro-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutyl]-methanol (172.6 mg, 0.475 mmol) in dioxane (3 mL) and iPrOH (3 mL) in a sealable glass tube, cooled by dry ice/acetone, until the volume increased by ≈2 mL, then the tube was sealed and heated to 90° C. overnight. The solvents were evaporated, water was added to the residue, and the pale yellow solid was filtered off and dried in vacuo to give the title compound as a pale yellow solid. The compound was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 2.41-2.52 (m, 2H), 2.52-2.64 (m, 3H), 3.83 (d, J=6.3 Hz, 2H), 5.30-5.40 (mc, 1H), 5.60 (brs, 2H), 7.29 (s, 1H), 8.26 (s, 1H). MS (ES+): m/z 345.1 (100) [MH+]. HPLC: tR=1.9 min (OpenLynx, polar—5 min).

Workup

  1. customcondensed
  2. temperatureincreased by ≈2 mL
  3. customthe tube was sealed
  4. customThe solvents were evaporated
  5. additionwater was added to the residue
  6. filtrationthe pale yellow solid was filtered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-8d945419a41749808d2f7d27cdd4f7a9
Source dataset
uspto-grants-2010_10
Patent number
US07820662B2

Reaction notes

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