HCID 86706946, compound → HCID 86706966, compound

HRID 1750296Notes

Reaction equation

I[C:2]1[C:10]2[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:3]=1[CH:25]=[O:26].ClC1C2C([C:37]3[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=3)[C:40]#[N:41])=C(C)N(COCC[Si](C)(C)C)C=2N=CN=1>>[CH:25]([C:3]1[N:4]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2[N:6]=[CH:7][N:8]=[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:10]=2[C:2]=1[C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[C:40]#[N:41])=[O:26]

Participants

Reactant 2

HCID 86706946HCID 86706946, compound

HCID 86706965HCID 86706965, compound

Product 1

HCID 86706966HCID 86706966, compound

Procedure

5-Iodo-4-(morpholin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde (C29) was converted to the product using the method described for synthesis of 3-(4-chloro-6-methyl-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile (C7) in Example 2. The product was obtained as a yellow solid. Yield: 1.5 g, 3.2 mmol, 78%. 1H NMR (400 MHz, CDCl3) δ 9.75 (s, 1H), 8.60 (s, 1H), 7.77-7.83 (m, 2H), 7.72-7.76 (m, 1H), 7.67 (br dd, J=8, 8 Hz, 1H), 6.09 (s, 2H), 3.66-3.71 (m, 2H), 3.38-3.44 (m, 4H), 3.23-3.28 (m, 4H), 0.94-1.01 (m, 2H), −0.03 (s, 9H).

Workup

customThe product was obtained as a yellow solid

Sources & evidence

ORD record: ord-1357c392c9bc430fb1283b0964e9291d
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156845B2

Reaction notes

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