Trifluoroacetic acid → 7-benzyl-N4-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

HRID 1805840Notes

Reaction equation

[CH2:1]([N:8]1[C:12]2[N:13]=[C:14]([NH2:18])[N:15]=[C:16](Cl)[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:21]=1[NH2:22].FC(F)(F)C(O)=O>FC(F)(F)CO>[CH2:1]([N:8]1[C:12]2[N:13]=[C:14]([NH2:18])[N:15]=[C:16]([NH:22][C:21]3[C:23]([CH3:28])=[CH:24][C:25]([CH3:27])=[CH:26][C:20]=3[CH3:19])[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 7-benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine (200 mg, 0.78 mmol) and 2,4,6-trimethylaniline (0.44 mL, 3.08 mmol) in 2,2,2-trifluoroethanol (4 mL) was added trifluoroacetic acid (0.48 mL, 6.24 mmol). The resulting solution was heated at 100° C. for 2 days and cooled to room temperature. The reaction was concentrated to brown oil and diluted with CH2Cl2 (30 mL). The organic solution was washed with aqueous NaHCO3 solution (20 mL) and brine (20 mL), dried with Na2SO4, and concentrated to dryness. Silica gel chromatography (CH2Cl2:MeOH=95:5) yielded 251 mg (90%) of 7-benzyl-N4-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine.

Workup

temperaturecooled to room temperature
concentrationThe reaction was concentrated to brown oil
additiondiluted with CH2Cl2 (30 mL)
washThe organic solution was washed with aqueous NaHCO3 solution (20 mL) and brine (20 mL)
dry with materialdried with Na2SO4
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-4d8057ab68ff425ab089572cd4ff350b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354532B2

Reaction notes

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