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

HRID 244177Notes

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

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 ≈1 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

customcondensed
temperatureincreased by ≈1 mL
customthe tube was sealed
customThe solvents were evaporated
additionwater was added
extractionthe mixture was extracted with CH2Cl2 (3×20 mL)
washthe combined CH2Cl2 extracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-48caa8a1575a4d64a506244c174b0e67
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653268B2

Reaction notes

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