Methyl 5-aminobenzofuran-2-carboxylate → 5-fluoro-N4-(3-isopropylphenyl)-N2-(2-methoxycarbonylbenzofur-5-yl)-2,4-pyrimidinediamine

HRID 733969Notes

Reaction equation

HRID 733969 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH3:17])[CH3:16])[CH:10]=2)[C:5]([F:18])=[CH:4][N:3]=1.[CH3:19][O:20][C:21]([C:23]1[O:24][C:25]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][C:26]=2[CH:27]=1)=[O:22]>>[F:18][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH3:17])[CH3:16])[CH:10]=2)=[N:7][C:2]([NH:32][C:29]2[CH:30]=[CH:31][C:25]3[O:24][C:23]([C:21]([O:20][CH3:19])=[O:22])=[CH:27][C:26]=3[CH:28]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 10845388Methyl 5-aminobenzofuran-2-carboxylateHCID 220603082-chloro-5-fluoro-N4-(3-isopropylphenyl)-4-pyrimidineamine

Product 1

HCID 220604465-fluoro-N4-(3-isopropylphenyl)-N2-(2-methoxycarbonylbenzofur-5-yl)-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-isopropylphenyl)-4-pyrimidineamine and 2-methoxycarbonyl-5-aminobenzofuran were reacted to give 5-fluoro-N4-(3-isopropylphenyl)-N2-(2-methoxycarbonylbenzofur-5-yl)-2,4-pyrimidinediamine. LCMS: retn, time: 26.05 min.; purity: 99%; MS (m/e): 420 (M+), 422 (MI+); 1H NMR (DMSO-d6): δ 10.00 (1H, s), 9.95 (1H, s), 8.31 (1H, d, J=4.8 Hz), 8.11 (1H, s), 7.74 (3H, m), 7.35 (1H, s), 7.35 (1H, t, J=7.2 Hz), 7.12 (1H, d, J=7.2 Hz), 3.99 (3H, s), 2.83 (1H, sept, J=6.9 Hz), 1.20 (6H, d, J=6.9 Hz).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-cb1fa5cc574c4240b63e21d3b8c270e3
Source dataset
uspto-grants-2009_09
Patent number
US07589200B2

Reaction notes

Loading…