Allyl bromide → 6-(2-Allyloxy-5-chloro-phenyl)-N4-(4-chloro-phenyl)-pyrimidine-2,4-diamine

HRID 28654Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[OH:15])[CH:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:3]=1.Br[CH2:25][CH:26]=[CH2:27]>>[CH2:27]([O:15][C:9]1[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:8]=1[C:6]1[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH:5]=1)[CH:26]=[CH2:25]

Participants

Reactant 2

HCID 7841Allyl bromide

HCID 136053632HCID 136053632, compound

Product 1

HCID 597882486-(2-Allyloxy-5-chloro-phenyl)-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamineYield 80%

Procedure

Following the method described in Example 165, 2-[2-amino-6-(4-chloro-phenylamino)-pyrimidin-4-yl]-4-chloro-phenol and 3-bromo-propene provided the title compound (80% yield) 1H NMR (DMSO-d6) δ 4.68 (d, 2H, CH2), 5.25-5.28 (m, 1H, Ar), 5.36-5.41 (m, 1H, Ar), 6.03-6.08 (m, 1H, Ar), 6.36 (s, 2H, NH2), 6.70 (s, 1H, Ar), 7.14 (d, 1H, J=8.9 Hz, Ar), 7.31 (d, 2H, J=8.9 Hz, Ar), 7.40 (dd, 1H, J—2.8 Hz, J=8.8 Hz, Ar), 7.78 (d, 2H, J=8.9 Hz, Ar), 7.85 (d, 1H, J=2.8 Hz, Ar), 9.32 (s, 1H, NH).

Sources & evidence

ORD record: ord-6a3e0e179c6b442a9d7a07fcbddd4462
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419984B2

Reaction notes

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