3-[4-(dimethylamino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile → HCID 86706941, compound

HRID 1750259Notes

Reaction equation

HRID 1750259 reaction equation
IC1C2C(N(C)C)=NC=NC=2N(COCC[Si](C)(C)C)C=1.ClC1C2C(I)=CN(COCC[Si](C)(C)C)C=2N=CN=1.CN(C)C1C2C(C3C=C(C=CC=3)C#N)=CNC=2N=CN=1.[N:61]1([C:67]2[C:68]3[C:75]([B:76]4[O:80][C:79]([CH3:82])([CH3:81])[C:78]([CH3:84])([CH3:83])[O:77]4)=[CH:74][N:73]([CH2:85][O:86][CH2:87][CH2:88][Si:89]([CH3:92])([CH3:91])[CH3:90])[C:69]=3[N:70]=[CH:71][N:72]=2)[CH2:66]COC[CH2:62]1>>[CH3:66][N:61]([CH3:62])[C:67]1[C:68]2[C:75]([B:76]3[O:80][C:79]([CH3:81])([CH3:82])[C:78]([CH3:84])([CH3:83])[O:77]3)=[CH:74][N:73]([CH2:85][O:86][CH2:87][CH2:88][Si:89]([CH3:92])([CH3:91])[CH3:90])[C:69]=2[N:70]=[CH:71][N:72]=1

Participants

5

Reactant 4

HCID 727068413-[4-(dimethylamino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrileHCID 867069334-chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidineHCID 86706934HCID 86706934, compoundHCID 86706942HCID 86706942, compound

Product 1

HCID 86706941HCID 86706941, compound

Procedure

5-Iodo-N,N-dimethyl-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-amine [C3, prepared from 4-chloro-5-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (C1) according to the method described for synthesis of 3-[4-(dimethylamino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile (5) in Example 5] was converted to the product according to the method described for synthesis of 4-(morpholin-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (P2) in Preparation P2. The product was obtained as a yellow solid. Yield: 342 mg, 0.817 mmol, 69%. LCMS m/z 419.3 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 7.57 (s, 1H), 5.56 (s, 2H), 3.49-3.57 (m, 2H), 3.25 (s, 6H), 1.36 (s, 12H), 0.86-0.94 (m, 2H), −0.06 (s, 9H).

Workup

  1. customThe product was obtained as a yellow solid

Sources & evidence

ORD record
ord-eeba23b206fa4932bba1690fd689d8be
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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