(6-Aminopyrimidin-4-yl)methanol → 3,5-Dichloro-4-[4-(6-hydroxymethyl-pyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]-benzonitrile

HRID 626690Notes

Reaction equation

HRID 626690 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:28])[C:9]=1[N:10]1[CH:27]=[C:13]2[C:14]([NH:18][C:19]3[CH:24]=[C:23]([CH3:25])[N:22]=[C:21](C)[N:20]=3)=[N:15][CH:16]=[CH:17][C:12]2=[N:11]1)[C:5]#[N:6].NC1N=CN=C(C[OH:37])C=1.ClC1C=C(C=C(Cl)C=1N1C=C2C(Cl)=NC=CC2=N1)C#N>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:28])[C:9]=1[N:10]1[CH:27]=[C:13]2[C:14]([NH:18][C:19]3[CH:24]=[C:23]([CH2:25][OH:37])[N:22]=[CH:21][N:20]=3)=[N:15][CH:16]=[CH:17][C:12]2=[N:11]1)[C:5]#[N:6]

Participants

4

Reactant 3

HCID 21934615(6-Aminopyrimidin-4-yl)methanolHCID 696715893,5-Dichloro-4-[4-(2,6-dimethylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitrileHCID 866970463,5-Dichloro-4-(4-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile

Product 1

HCID 696713413,5-Dichloro-4-[4-(6-hydroxymethyl-pyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]-benzonitrileYield 37%

Procedure

Following the procedure described for 3,5-dichloro-4-[4-(2,6-dimethylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitrile, (6-amino-pyrimidin-4-yl)-methanol and 3,5-dichloro-4-(4-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile were reacted to afford the title compound as a pale yellow solid (70 mg, 37% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.76 (s, 1H), 9.22 (s, 1H), 8.70 (s, 2H), 8.49 (s, 2H), 8.00 (d, J=6.4 Hz, 1H), 7.25-7.22 (m, 1H), 5.61 (t, J=5.7 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H). LCMS (Method D): RT=2.05 min, m/z: 412 [M+H+].

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9c020ef76f7d4f8e9e36b432d1b5f4b7
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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