2-Methyl-6-(methylsulfonyl)pyridin-3-amine → tert-Butyl 4-(4-(2-methyl-6-(methylsulfonyl)pyridin-3-ylamino)-6H-pyrimido[5,4-b][1,4]oxazin-8(7H)-yl)piperidine-1-carboxylate

HRID 604347Notes

Reaction equation

HRID 604347 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([S:9]([CH3:12])(=[O:11])=[O:10])[N:3]=1.Cl[C:14]1[C:19]2[O:20][CH2:21][CH2:22][N:23]([CH:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)[C:18]=2[N:17]=[CH:16][N:15]=1>>[CH3:1][C:2]1[C:7]([NH:8][C:14]2[C:19]3[O:20][CH2:21][CH2:22][N:23]([CH:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]4)[C:18]=3[N:17]=[CH:16][N:15]=2)=[CH:6][CH:5]=[C:4]([S:9]([CH3:12])(=[O:11])=[O:10])[N:3]=1

Participants

3

Reactant 2

HCID 510505272-Methyl-6-(methylsulfonyl)pyridin-3-amineHCID 58293623tert-butyl 4-(4-chloro-6H-pyrimido[5,4-b][1,4]oxazin-8(7H)-yl)piperidine-1-carboxylate

Product 1

HCID 58293644tert-Butyl 4-(4-(2-methyl-6-(methylsulfonyl)pyridin-3-ylamino)-6H-pyrimido[5,4-b][1,4]oxazin-8(7H)-yl)piperidine-1-carboxylate

Procedure

By the procedure described in Example 3, with the exception that 2-methyl-6-(methylsulfonyl)pyridin-3-amine was used instead of 2-fluoro-4-(methylsulfonyl)-aniline, tert-butyl 4-(4-chloro-6H-pyrimido[5,4-b][1,4]oxazin-8(7H)-yl)piperidine-1-carboxylate from Example 3C was converted into Example 123. 1H NMR (500 MHz, CDCl3) δ ppm 1.45 (s, 9H) 1.55-1.65 (m, 2H) 1.66-1.72 (m, 2H) 2.61 (s, 3H) 2.82-2.90 (m, 2H) 3.15 (s, 3H) 3.45-3.48 (m, 2H) 4.25-4.28 (m, 4H) 4.79-4.88 (m, 1H) 6.86-7.00 (m, 1H) 7.91 (d, J=8.25 Hz, 1H) 8.06 (s, 1H) 8.91 (m, 1H) LRMS (ESI): 505.3 [M+H]+.

Sources & evidence

ORD record
ord-d52fe56acc844f1f8b114a91211ceca7
Source dataset
uspto-grants-2011_03
Patent number
US07910583B2

Reaction notes

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