Ammonia → 7-cyclopropylmethyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

HRID 386253Notes

Reaction equation

HRID 386253 reaction equation
[NH3:1].Cl[C:3]1[C:4]2[C:11]([I:12])=[CH:10][N:9]([CH2:13][CH:14]3[CH2:16][CH2:15]3)[C:5]=2[N:6]=[CH:7][N:8]=1.C(=O)=O.CC(C)=O>O1CCOCC1.CC(O)C>[CH:14]1([CH2:13][N:9]2[C:5]3[N:6]=[CH:7][N:8]=[C:3]([NH2:1])[C:4]=3[C:11]([I:12])=[CH:10]2)[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 18522661Acetone cardiceHCID 576808904-Chloro-7-cyclopropylmethyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 576808977-cyclopropylmethyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Gaseous ammonia (from a lecture bottle) was condensed into a suspension of 4-chloro-7-cyclopropylmethyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (394.8 mg, 1.184 mmol) in dioxane (3 mL) and iPrOH (2 ml.) in a sealable glass tube, cooled by dry ice/acetone, until the volume increased by mL, then the tube was sealed and heated to 100° C. overnight. The solvents were evaporated, water was added, the mixture was extracted with CH2Cl2 (3×20 mL), and the combined CH2Cl2 extracts were washed with brine, dried over MgSO4, filtered and concentrated to give the title compound as a white solid. 1H NMR (CDCl3, 400 MHz): δ=0.36-0.43 (m, 2H), 0.58-0.66 (m, 2H), 1.19-1.29 (m, 1H), 4.03 (d, J=6.8 Hz, 2H), 5.63 (brs, 2H), 7.19 (s, 1H), 8.27 (s, 1H). 13C NMR (CDCl3, 100.6 MHz, DEPT135): δ=4.02 (2C, −), 11.28 (+), 48.46 (Cquart), 49.19 (−), 103.96 (Cquart), 128.70 (+), 150.03 (Cquart), 152.05 (+), 156.88 (Cquart). MS (ES+): m/z 315.1 (100) [MH+]. HPLC: tR=2.3 min (OpenLynx, polar—5 min).

Workup

  1. customcondensed
  2. temperatureincreased by mL
  3. customthe tube was sealed
  4. customThe solvents were evaporated
  5. additionwater was added
  6. extractionthe mixture was extracted with CH2Cl2 (3×20 mL)
  7. washthe combined CH2Cl2 extracts were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-814a6fa50f144631bac3c81620ecbfde
Source dataset
uspto-grants-2013_02
Patent number
US08367826B2

Reaction notes

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