6-Chloro-8-oxa-3,5-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),3,5,10,12-hexaene → N4-[2-([1]benzofuro[3,2-d]pyrimidin-4-ylamino)ethyl]pyrimidine-2,4-diamine

HRID 2386999Notes

Reaction equation

HRID 2386999 reaction equation
Cl[C:2]1[C:3]2[O:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[C:4]=2[N:5]=[CH:6][N:7]=1.Cl.Cl.[NH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([NH2:27])[N:22]=1>>[N:5]1[C:4]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[O:10][C:3]=2[C:2]([NH:17][CH2:18][CH2:19][NH:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH2:27])[N:22]=2)=[N:7][CH:6]=1

Participants

3

Reactant 2

HCID 6092956-Chloro-8-oxa-3,5-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),3,5,10,12-hexaeneHCID 86638141N4-(2-aminoethyl)pyrimidine-2,4-diamine dihydrochloride

Product 1

HCID 44609562N4-[2-([1]benzofuro[3,2-d]pyrimidin-4-ylamino)ethyl]pyrimidine-2,4-diamine

Procedure

4-Chloro-benzo[4,5]furo[3,2-d]pyrimidine (50 mg, 0.244 mmol) and the product of Example 1E (72 mg, 0.318 mmol) were treated under the conditions of Example 1F to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.59-3.85 (m, 4H) 6.03 (d, J=7.12 Hz, 1H) 7.52 (t, J=7.46 Hz, 1H) 7.58-7.67 (m, 1H) 7.67-7.88 (m, 4H) 8.11 (d, J=7.12 Hz, 1H) 8.28-8.44 (m, 1H) 8.82 (t, J=5.43 Hz, 1H) 11.69 (s, 1H); MS (ESI+) m/z 322.0 (M+H)+.

Sources & evidence

ORD record
ord-5bec58ecc754492f840980aee74bef58
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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