Dimethylacetamide → HCID 178493096, compound

HRID 415415Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:19][C:20]2[CH:24]=[C:23]([O:25][CH3:26])[NH:22][N:21]=2)=[N:4][C:5]([NH:9][C@H:10]([C:12]2[N:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)[CH3:11])=[N:6][C:7]=1Cl.C[C:28]([N:30](C)C)=O>[Zn].[C-]#N.[Zn+2].[C-]#N.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[C:7]([C:28]#[N:30])=[N:6][C:5]([NH:9][C@H:10]([C:12]2[N:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)[CH3:11])=[N:4][C:3]=1[NH:19][C:20]1[CH:24]=[C:23]([O:25][CH3:26])[NH:22][N:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5,6-dichloro-N2-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]-N4-(5-methoxy-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (Example 30, 100 mg), zinc (17 mg), zinc cyanide (31 mg), DPPF (7 mg) and Pd2(dba)3 (12 mg) in DMA (2.0 ml) was degassed and heated at 100° C. for 2 hours. The solution was separated between ethyl acetate and water. Organic solvent was removed under reduced pressure and the residue was purified by Gilson (10-50% MeCN/H2O, 15 minutes) to give the titled compound as solid (42.5 mg). 1H NMR δ 10.20 (s, 1H) 8.89 (s, 2H) 8.56 (bs, 1H) 5.63 (s, 1H) 5.03-5.29 (m, 1H) 3.75 (s, 3H) 1.47 (d, 3H); m/z 390.

Workup

customwas degassed
customThe solution was separated between ethyl acetate and water
customOrganic solvent was removed under reduced pressure
customthe residue was purified by Gilson (10-50% MeCN/H2O, 15 minutes)

Sources & evidence

ORD record: ord-98210061009c42e3bce1be8924684e55
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088784B2

Reaction notes

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