4-Chloro-6-methylpyrimidine → HCID 59239536, compound

HRID 1697952Notes

Reaction equation

HRID 1697952 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[C:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21][C:22]=3[N:23]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].Cl[C:32]1[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34][N:33]=1>>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[C:16]3[CH2:17][CH2:18][N:19]([C:32]4[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34][N:33]=4)[CH2:20][CH2:21][C:22]=3[N:23]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 5817964-Chloro-6-methylpyrimidineHCID 59239074HCID 59239074, compound

Product 1

HCID 59239536HCID 59239536, compoundYield 36%

Procedure

The compound op was prepared following the general procedure in Example 2, substituting 1-ethyl-3-(4-(4-morpholino-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea with (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-6,7,8,9-tetrahydro-5H-pyrimido[5,4-d]azepin-2-yl)phenyl)urea and substituting 2-Chloropyrimidine with 4-Chloro-6-methylpyrimidine. The desired product op (36% yield) was obtained as white powder: 1H NMR (500 MHz, DMSO) δ 8.70 (s, 1H), 8.42 (s, 1H), 8.20 (d, J=8.8 Hz, 2H), 7.49 (d, J=8.8 Hz, 2H), 6.80 (s, 1H), 6.19 (t, J=5.5 Hz, 1H), 4.10-3.62 (m, 9H), 3.52 (dd, J=11.0, 3.6 Hz, 1H), 3.21-3.02 (m, 5H), 2.88 (m, 2H), 2.28 (s, 3H), 1.12 (d, J=6.4 Hz, 3H), 1.06 (t, J=7.2 Hz, 3H); LC-MS m/z=503 (M+H).

Workup

  1. customThe compound op was prepared

Sources & evidence

ORD record
ord-7a9baebe10db45e68523d2261322c8e8
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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