Methyl 5-aminobenzofuran-2-carboxylate → 5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-N4-(4-isopropoxyphenyl)-2,4-pyrimidinediamine

HRID 71439Notes

Reaction equation

HRID 71439 reaction equation
C1COC2C=CC(NC3C(F)=CN=C(NC4C=CC=C(O)C=4)N=3)=CC=2O1.Cl[C:28]1[N:33]=[C:32]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH:42]([CH3:44])[CH3:43])=[CH:37][CH:36]=2)[C:31]([F:45])=[CH:30][N:29]=1.[CH3:46][O:47][C:48]([C:50]1[O:51][C:52]2[CH:58]=[CH:57][C:56]([NH2:59])=[CH:55][C:53]=2[CH:54]=1)=[O:49]>>[F:45][C:31]1[C:32]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH:42]([CH3:44])[CH3:43])=[CH:37][CH:36]=2)=[N:33][C:28]([NH:59][C:56]2[CH:57]=[CH:58][C:52]3[O:51][C:50]([C:48]([O:47][CH3:46])=[O:49])=[CH:54][C:53]=3[CH:55]=2)=[N:29][CH:30]=1

Participants

4

Reactant 3

HCID 10845388Methyl 5-aminobenzofuran-2-carboxylateHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamineHCID 220607632-chloro-5-fluoro-N-(4-isopropoxyphenyl)-4-pyrimidineamine

Product 1

HCID 220603265-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-N4-(4-isopropoxyphenyl)-2,4-pyrimidinediamine

Procedure

In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-[4-(isopropoxy)phenyl]-4-pyrimidineamine and 2-methoxycarbonyl-5-aminobenzofuran were reacted to yield 5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-N4-(4-isopropoxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.04 (d, 1H, J=1.8 Hz), 7.49-7.41 (m, 4H), 7.35 (dd, 1H, J=2.4 and 8.7 Hz), 7.14 (bs, 1H), 6.90 (d, 2H, J=9.3 Hz), 6.70 (bs, 1H), 4.56 (2q, 1H, J=5.7 Hz), 3.98 (s, 3H), 1.37 (d, 6H, J=5.7 Hz); LCMS: ret. time: 25.52 min.; purity: 98%; MS (m/e): 437 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ea120ea982164e4a84c6d8bedba2917e
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Reaction notes

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